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BOS - CHI

$26 Find cheap flights from Boston to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Boston to Chicago departing on 6/5. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Sat 6/22
Sat 6/29

Search hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Boston to Chicago.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Boston to Chicago.
In the last 7 days travelers have searched 43,800,826 times on KAYAK, and here is why:

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Cheap flight deals from Boston to Chicago (BOS-CHI)

 
These are the cheapest deals for flights from Boston to Chicago currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Boston to Chicago

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Boston to Chicago.

Recent one-way flight deals from Boston to Chicago

Only flying one-way? Below are some of the best one-way flight deals from Boston to Chicago found on KAYAK recently.

Recent last minute flight deals from Boston to Chicago

Leaving soon but still want a bargain? Check out these latest deals for last minute flights from Boston to Chicago.

Recent direct flight deals from Boston to Chicago

The latest deals for direct flights from Boston to Chicago so you can sit back and relax without the need for a layover.

Cheap bus & train deals from Boston to Chicago

Find recent round-trip train or bus tickets from Boston to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
7:49 am - 1:32 pmBOS-MDW
6h 43m1 stop
10:16 pm - 6:58 amMDW-BOS
7h 42m1 stop
$124Frontier
Find Deal
Wed, Jun 5 - Tue, Jun 11
7:49 am - 1:32 pmBOS-MDW
6h 43m1 stop
10:16 pm - 6:58 amMDW-BOS
7h 42m1 stop
$126Frontier
Find Deal
Wed, Jun 5 - Tue, Jun 11
2:40 pm - 4:32 pmBOS-ORD
2h 52mnonstop
8:00 am - 11:12 amORD-BOS
2h 12mnonstop
$147Delta
Find Deal
Tue, Aug 13 - Sat, Aug 17
4:25 pm - 6:20 pmBOS-ORD
2h 55mnonstop
7:17 pm - 10:43 pmORD-BOS
2h 26mnonstop
$157JetBlue
Find Deal
Wed, Jun 5 - Sat, Jun 8
6:10 am - 8:04 amBOS-ORD
2h 54mnonstop
8:40 am - 12:09 pmORD-BOS
2h 29mnonstop
$160JetBlue
Find Deal
Sat, Jun 1 - Wed, Jun 5
7:35 am - 9:27 amBOS-ORD
2h 52mnonstop
6:30 am - 9:58 amORD-BOS
2h 28mnonstop
$183Delta
Find Deal
Thu, Jun 13 - Sun, Jun 16
3:19 pm - 5:10 pmBOS-ORD
2h 51mnonstop
9:45 pm - 1:20 amORD-BOS
2h 35mnonstop
$227United Airlines
Find Deal
Wed, May 29 - Mon, Jun 3
6:00 am - 7:50 amBOS-ORD
2h 50mnonstop
9:45 pm - 1:20 amORD-BOS
2h 35mnonstop
$228United Airlines
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Thu, Jun 6 - Mon, Jun 10
7:05 pm - 11:59 pmBOS-ORD
5h 54m1 stop
3:27 pm - 6:44 pmORD-BOS
2h 17mnonstop
$275American Airlines
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Sun, May 26 - Wed, May 29
5:37 pm - 7:31 pmBOS-ORD
2h 54mnonstop
3:27 pm - 6:44 pmORD-BOS
2h 17mnonstop
$287American Airlines
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Sun, May 26 - Fri, May 31
11:28 am - 7:12 pmBOS-ORD
8h 44m1 stop
$26Spirit Airlines
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Wed, Jun 5
7:00 am - 8:33 amBOS-ORD
2h 33mnonstop
$30Spirit Airlines
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Wed, Aug 21
6:00 am - 7:54 amBOS-ORD
2h 54mnonstop
$58JetBlue
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Sun, Jun 16
5:14 am - 9:50 amBOS-ORD
5h 36m1 stop
$67JetBlue
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Tue, Jun 25
5:15 am - 7:11 amBOS-ORD
2h 56mnonstop
$69American Airlines
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Wed, Jul 17
5:18 am - 7:13 amBOS-ORD
2h 55mnonstop
$88American Airlines
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Sat, Jun 15
5:50 am - 7:36 amBOS-ORD
2h 46mnonstop
$89United Airlines
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Sun, Jul 14
6:00 am - 7:50 amBOS-ORD
2h 50mnonstop
$122United Airlines
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Fri, Jul 12
7:30 pm - 9:27 pmBOS-ORD
2h 57mnonstop
$124Delta
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Fri, Jun 14
6:25 am - 8:20 amBOS-ORD
2h 55mnonstop
$134Delta
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Thu, May 30
10:40 am - 9:55 amBOS-ORD
24h 15m3 stops
6:40 pm - 11:00 pmORD-BOS
27h 20m3 stops
$160Spirit Airlines
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Tue, May 28 - Tue, Jun 4
12:32 pm - 7:45 pmBOS-MDW
8h 13m1 stop
10:02 pm - 7:29 amMDW-BOS
8h 27m1 stop
$178Frontier
Find Deal
Sun, May 26 - Mon, Jun 3
8:50 am - 10:47 amBOS-ORD
2h 57mnonstop
3:27 pm - 6:44 pmORD-BOS
2h 17mnonstop
$197American Airlines
Find Deal
Tue, May 28 - Fri, May 31
4:25 pm - 6:20 pmBOS-ORD
2h 55mnonstop
5:35 pm - 11:09 pmORD-BOS
4h 34m1 stop
$200JetBlue
Find Deal
Tue, May 28 - Sat, Jun 1
8:50 am - 10:47 amBOS-ORD
2h 57mnonstop
3:20 pm - 9:00 pmORD-BOS
4h 40m1 stop
$225American Airlines
Find Deal
Tue, May 28 - Fri, May 31
10:08 am - 4:45 pmBOS-ORD
7h 37m1 stop
8:40 am - 12:09 pmORD-BOS
2h 29mnonstop
$241JetBlue
Find Deal
Tue, May 28 - Tue, Jun 4
4:45 pm - 6:37 pmBOS-ORD
2h 52mnonstop
6:04 am - 9:24 amORD-BOS
2h 20mnonstop
$247United Airlines
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Tue, May 28 - Tue, Jun 4
5:00 pm - 8:55 pmBOS-ORD
4h 55m1 stop
8:00 am - 11:12 amORD-BOS
2h 12mnonstop
$257Delta
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Sat, May 25 - Sat, Aug 17
2:10 pm - 4:04 pmBOS-ORD
2h 54mnonstop
5:15 pm - 8:44 pmORD-BOS
2h 29mnonstop
$267Delta
Find Deal
Tue, May 28 - Sat, Jun 1
8:45 am - 1:15 pmBOS-ORD
5h 30m1 stop
7:46 am - 11:17 amORD-BOS
2h 31mnonstop
$272United Airlines
Find Deal
Tue, May 28 - Thu, May 30
6:30 am - 8:24 amBOS-ORD
2h 54mnonstop
9:10 pm - 12:38 amORD-BOS
2h 28mnonstop
$40Spirit Airlines
Find Deal
Tue, Jun 11 - Tue, Jun 11
7:00 am - 8:33 amBOS-ORD
2h 33mnonstop
9:04 pm - 12:22 amORD-BOS
2h 18mnonstop
$50Spirit Airlines
Find Deal
Thu, Aug 22 - Tue, Aug 27
6:00 am - 7:54 amBOS-ORD
2h 54mnonstop
8:30 am - 11:56 amORD-BOS
2h 26mnonstop
$115JetBlue
Find Deal
Sun, Jun 16 - Tue, Jun 18
6:10 am - 8:04 amBOS-ORD
2h 54mnonstop
9:00 am - 12:33 pmORD-BOS
2h 33mnonstop
$136JetBlue
Find Deal
Wed, Jun 5 - Wed, Jun 12
5:18 am - 7:13 amBOS-ORD
2h 55mnonstop
8:36 pm - 12:01 amORD-BOS
2h 25mnonstop
$145American Airlines
Find Deal
Sat, Jun 15 - Tue, Jun 18
2:40 pm - 4:32 pmBOS-ORD
2h 52mnonstop
8:00 am - 11:12 amORD-BOS
2h 12mnonstop
$147Delta
Find Deal
Tue, Aug 13 - Sat, Aug 17
6:00 am - 7:50 amBOS-ORD
2h 50mnonstop
6:04 am - 9:24 amORD-BOS
2h 20mnonstop
$161United Airlines
Find Deal
Fri, Jun 14 - Sun, Jun 16
6:25 am - 8:20 amBOS-ORD
2h 55mnonstop
6:30 am - 9:58 amORD-BOS
2h 28mnonstop
$170Delta
Find Deal
Tue, Jun 4 - Tue, Jun 11
5:25 am - 7:17 amBOS-ORD
2h 52mnonstop
6:55 pm - 10:25 pmORD-BOS
2h 30mnonstop
$180American Airlines
Find Deal
Sun, Jun 2 - Tue, Jun 4
6:00 am - 7:50 amBOS-ORD
2h 50mnonstop
9:45 pm - 1:20 amORD-BOS
2h 35mnonstop
$182United Airlines
Find Deal
Tue, Jun 18 - Wed, Jun 19
4:45 pm - 7:50 pmBoston South Station-
Chicago Union
28h 05mnonstop
4:30 pm - 10:00 pmChicago Union-
Boston South Station
28h 30mnonstop
$170Greyhound
Find Deal
Wed, May 29 - Sat, Jun 1
7:25 pm - 11:55 pmBoston Allston-
Chicago Union
29h 30mnonstop
4:30 pm - 5:10 amChicago Union-
Boston Allston
35h 40mnonstop
$183FlixBus, Greyhound
Find Deal
Wed, May 29 - Sat, Jun 1
4:45 pm - 7:50 pmBoston South Station-
Chicago Union
28h 05mnonstop
1:45 am - 12:25 pmChicago Union-
Boston South Station
33h 40mnonstop
$184Greyhound
Find Deal
Wed, May 29 - Fri, May 31
7:45 pm - 10:40 pmBoston South Station-
Chicago Union
27h 55mnonstop
1:45 am - 12:25 pmChicago Union-
Boston South Station
33h 40mnonstop
$196Greyhound
Find Deal
Fri, Jun 7 - Thu, Jul 4
7:45 pm - 10:40 pmBoston South Station-
Chicago Union
27h 55mnonstop
11:30 am - 3:15 pmChicago Union-
Boston South Station
26h 45mnonstop
$196FlixBus, Greyhound
Find Deal
Fri, Jun 7 - Fri, Jul 5
12:57 pm - 10:12 amBoston Back Bay-
Chicago Union
22h 15mnonstop
9:30 pm - 8:24 pmChicago Union-
Boston Back Bay
21h 54mnonstop
$235Amtrak
Find Deal
Wed, Jul 3 - Mon, Jul 8
12:50 pm - 10:12 amBoston South Station-
Chicago Union
22h 22mnonstop
9:30 pm - 8:32 pmChicago Union-
Boston South Station
22h 02mnonstop
$235Amtrak
Find Deal
Wed, Jul 3 - Mon, Jul 8
12:57 pm - 10:12 amBoston Back Bay-
Chicago Union
22h 15mnonstop
9:30 pm - 8:24 pmChicago Union-
Boston Back Bay
21h 54mnonstop
$235Amtrak
Find Deal
Wed, Jul 3 - Mon, Jul 8
12:50 pm - 10:12 amBoston South Station-
Chicago Union
22h 22mnonstop
9:30 pm - 8:32 pmChicago Union-
Boston South Station
22h 02mnonstop
$235Amtrak
Find Deal
Wed, Jul 3 - Mon, Jul 8
12:57 pm - 10:12 amBoston Back Bay-
Chicago Union
22h 15mnonstop
9:30 pm - 8:24 pmChicago Union-
Boston Back Bay
21h 54mnonstop
$263Amtrak
Find Deal
Tue, Jul 9 - Sun, Jul 14

Flights from Boston to Chicago - Travel Insights & Trends

Get data-powered insights and trends into flights from Boston to Chicago to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Boston to Chicago flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for one-way flights from Boston to Chicago.
Our data shows that the cheapest route for a one-way flight from Boston to Chicago cost $86 and was between Boston and Chicago O'Hare Intl Airport. On average, the best prices are found if you fly from Boston to Chicago Midway Airport. The average price for a return flight for this route is $140.

What’s the cheapest day of the week to fly from Boston to Chicago?

The average price of all flights from Boston to Chicago clicked on KAYAK for each day over the last 12 months.
When flying from Boston to Chicago, you should consider leaving on a Tuesday and avoid Fridays if you are looking for the best rates. For your return to Boston, you’ll find the best rates on Tuesdays and the most expensive ones on Mondays.

What is the cheapest month to fly from Boston to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Boston to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from Boston to Chicago is January, where tickets cost $187 on average. On the other hand, the most expensive months are June and July, where the average cost of tickets is $327 and $311 respectively.

How far in advance should I book a flight from Boston to Chicago?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Boston to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Boston to Chicago, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 65 days before departure.

Which airlines provide the cheapest flights from Boston to Chicago?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the last 72 hours, the best return deals on flights connecting Boston to Chicago were found on Frontier ($124) and Spirit Airlines ($139). Spirit Airlines proposed the cheapest one-way flight at $26.

Which airlines fly most frequently between Boston and Chicago?

American Airlines connects Boston to Chicago with up to 8 flights per day and both Delta and Southwest also offer 8 flights per day.

Which airlines fly non-stop between Boston and Chicago?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from Boston to Chicago.
There are 6 airlines that fly nonstop from Boston to Chicago. They are: American Airlines, Delta, JetBlue, Southwest, Spirit Airlines and United Airlines. The cheapest price of all airlines flying this route was found with Spirit Airlines at $56 for a one-way flight. On average, the best prices for this route can be found at Spirit Airlines.

How many flights are there between Boston and Chicago per day?

Each day, there are between 35 and 43 nonstop flights that take off from Boston and land in Chicago, with an average flight time of 2h 50m. The most common departure time is 4:00 pm and most flights take off in the morning, while the most flights land at Chicago O'Hare Intl Airport. Each week, there are 273 flights. The most frequent day of departure is Thursday, when 16% of all weekly flights depart. The fewest flights depart on a Saturday.

Which cabin class options are there for flights between Boston and Chicago?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There are 4 cabin class options for the route. These are First, Business, Economy and Prem Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

How long does a flight from Boston to Chicago take?

The duration of a nonstop flight to Chicago from Boston is typically 2h 33m. The journey crosses a distance of 850 miles.

What’s the earliest departure time from Boston to Chicago?

Early birds can take the earliest flight from Boston at 5:00 am and will be landing in Chicago at 6:55 am.

What’s the latest departure time from Boston to Chicago?

If you prefer to fly at night, the latest flight from Boston to Chicago jets off at 9:55 pm and lands at 11:30 pm.

Good to know

Low season

January

High season

May

Cheapest flight

$26
Best time to beat the crowds with an average 32% drop in price.
Most popular time to fly with an average 11% increase in price.
Flight from Boston to Chicago O'Hare Airport

When to book flights from Boston to Chicago

Are your dates flexible? Find out the best times to travel from Boston to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Boston to Chicago

  • What are the most sustainable airlines with Boston to Chicago flights?

    Porter Airlines, United Airlines, and American Airlines offer some of the most environmental-friendly flights to Chicago from Boston. Their flights emit about 48%, 46%, and 42% less carbon respectively than their competitors. Those looking to fly more sustainably from Boston to Chicago should prioritize nonstop flights, embrace the use of renewable plastics, and pack light for the trip.

  • What are the parking options at Boston Logan International Airport?

    If you’ll be driving to the airport, you’ll be happy to know that BOS offers convenient onsite parking options. Parking is available in Central Parking Garage, Economy Garage, and the Terminal B Garage. All the parking garages are easily accessible from the terminals by the moving sidewalks and walkways. Additionally, the airport partners with other agencies to offer multiple secure offsite parking options.

  • What accessible services are offered at Boston Logan International Airport?

    BOS provides Braille and Emergency Call keys in elevators. All restrooms within the airport are accessible, and it also provides restrooms for the companions. To enhance transit for passengers with reduced mobility, BOS provides Massport Shuttles. These buses are free, are equipped with wheelchair lifts, and use visual and audio assistance systems to announce the bus stops. All airlines flying through BOS also run wheelchair assistance services.

  • Are there nursing rooms at Chicago O’Hare International Airport?

    Yes, ORD provides Mother's Rooms in every terminal. The rooms offer a space for traveling mothers to breastfeed or pump and are equipped with a sink, comfortable seats, power outlets, and diaper changing tables. The rooms are available near Gate B10 on Concourse B in Terminal 1. In Terminal 2, they are by Gates E5 and F9. Others are also near Gate L6 in Terminal 3, and Gate 20 in Terminal 5.

  • If I want to use mass transit to get to Boston Logan International Airport, what is my best choice?

    The Blue Line Subway is an excellent choice for quick and reliable transportation to the airport. Save the headaches of traffic by taking the MBTA Blue Line to the station at the airport and then simply board one of the free shuttle buses to all of the airport terminal buildings.

  • Are there pet relief areas at Boston Logan International Airport?

    The pet relief areas at Boston Logan International Airport are located on the arrivals level of every terminal building. In addition, there is a pet relief area located in Terminal E near gate E7. Keep in mind that this is the only pet relief area that is past security.

  • If I am being picked up at Chicago O'Hare International Airport, where is the best place to meet my ride?

    Passengers can be picked up curbside on the lower level. As a reminder, there is no parking at the terminal building at any time. It is advisable to use the cell phone lot that is provided at the airport to wait for arriving passengers rather than just circling the airport.

  • Where can I rent a car at Chicago O'Hare International Airport?

    The airport offers a complimentary shuttle to the airport's Multi-Modal Facility, where all on-site car rental companies are located. Travelers can pick up the shuttle by exiting the Lower Level Baggage Claim and boarding the shuttle bus at the curb front. Each terminal has a designated pickup area outside the building.

  • What is the cheapest flight from Boston to Chicago?

    In the last 3 days, the lowest price for a flight from Boston to Chicago was $26 for a one-way ticket and $124 for a round-trip.

  • Do I need a passport to fly between Boston and Chicago?

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

  • Which airports will I be using when flying from Boston to Chicago?

    When flying out of Boston you will be using Boston Logan Intl. You will be landing at one of these airports: Chicago Midway or Chicago O'Hare Intl.

  • Which airlines offer Wi-Fi service onboard planes from Boston to Chicago?

    American Airlines, JetBlue, Delta, Alaska Airlines, and Aeromexico offer inflight Wi-Fi service on the Boston to Chicago flight route.

  • Which aircraft models fly most regularly from Boston to Chicago?

    The Boeing 737-800 is the aircraft model that flies most regularly on the Boston to Chicago flight route.

  • Which airline alliances offer flights from Boston to Chicago?

    oneworld, Star Alliance, and SkyTeam are the airline alliances operating flights between Boston and Chicago, with oneworld being the most commonly used for this route.

  • On which days can I fly direct from Boston to Chicago?

    There are nonstop flights from Boston to Chicago on a daily basis.

  • Which is the best airline for flights from Boston to Chicago, Delta or JetBlue?

    The two airlines most popular with KAYAK users for flights from Boston to Chicago are Delta and JetBlue. With an average price for the route of $273 and an overall rating of 8.0, Delta is the most popular choice. JetBlue is also a great choice for the route, with an average price of $248 and an overall rating of 7.6.

  • How does KAYAK find such low prices on flights from Boston to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Boston to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Boston to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Boston is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Boston to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Boston with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Boston to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Boston up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding a cheap flight from Boston to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $134 or less one-way and $257 or less round-trip.
  • Consider booking flights with at least a single stop en route if you want to fly more affordably from Boston to Chicago. These flights have different stopover options depending on your airline and arrival airport. Spirit Airlines, American Airlines, and Delta have common stops in Philadelphia, Detroit, Myrtle Beach, Washington, and LaGuardia Airport.
  • Flights from Boston to Chicago arrive at either O’Hare International Airport (ORD) or Chicago Midway International Airport (MDW). Of the two, ORD stands out as the best airport to fly into. It serves most of the direct flights from Boston and also has good connections to various transportation forms.
  • Travelers with kids will be glad to learn that Boston Logan International Airport (BOS) has Kidports where their kids can steam off before catching their flight. They are near Gate 18 in Terminal A, and by Gate 25 in Terminal C. In Terminal B, they are between Gates B30 and B36.
  • If you need cash before flying out from BOS, visit the ATMs at the airport. Citizens Bank, Chase, and Bank of America operate ATMs in the Departures area in Terminal A. ATMs are also available in various locations in Terminals B, C, and E.
  • Passengers flying to ORD are welcome to use the charging stations at the airport. You can find the charging stations by Gates B19, B15, B14, B11, and B4 in Terminal 1. In Terminal 2, you will find the charging ports by Gates C28, C21, C15, C7, E7, and F2B.
  • Before your flight from Boston to Chicago, be sure to get a taste of some excellent seafood at Legal's Test Kitchen. This restaurant features an all-day menu, but its specialties are its seafood-inspired dishes like shrimp cocktail and a variety of clam chowders. Located in Terminal A of Boston Logan International Airport, this is a perfect spot to get that last New England-style seafood meal before your flight to the Midwest.
  • There may be nothing that says Boston better than Wahlburgers. Founded and operated by the iconic Wahlberg family, this burger joint is known for its oversized burgers and outrageous onion rings. They are located in Terminal C of Boston Logan International Airport, and they make a great spot to grab a burger and beer before your flight from Boston to Chicago.
  • Flights from Boston to Chicago can be stressful. Why not slow down for a few minutes before your flight with a chair massage or a manicure at BeRelax? Located in Terminal C near Gare C-25 at Boston Logan International Airport, BeRelax also offers waxing and facial care to give you your best look and most relaxed self before your flight.
  • Travelers on flights from Boston to Chicago looking for a convenient hotel need look no further than the Hilton Chicago O'Hare Airport. This on-site property is excellent for business travelers who do not want to bother with the hassle of downtown hotels. The hotel features an indoor pool, an excellent restaurant for steaks and seafood, and a lively sports bar.
  • When looking for a hotel that is conveniently located close to Chicago Midway airport, the Chicago Marriott Midway is an excellent choice. They offer a 24-hour airport shuttle, tasteful decor, an indoor pool, tons of meeting space, a fitness center, wireless internet access, and even a Starbucks coffee shop.
See more tips

Prefer to fly non-stop from Boston to Chicago?

Find which airlines fly direct from Logan Intl to Chicago, which days they fly and book direct flights.

Nonstop departures

Boston Logan Intl to Chicago

Monday

ANA, Air New Zealand, Alaska Airlines, +22 more

ANA, Air New Zealand, +23 more

Tuesday

ANA, Air New Zealand, Alaska Airlines, +20 more

ANA, Air New Zealand, +21 more

Wednesday

ANA, Air New Zealand, Alaska Airlines, +22 more

ANA, Air New Zealand, +23 more

Thursday

ANA, Air New Zealand, Alaska Airlines, +22 more

ANA, Air New Zealand, +23 more

Friday

ANA, Air New Zealand, Alaska Airlines, +22 more

ANA, Air New Zealand, +23 more

Saturday

ANA, Air New Zealand, Alaska Airlines, +21 more

ANA, Air New Zealand, +22 more

Sunday

ANA, Air New Zealand, Alaska Airlines, +23 more

ANA, Air New Zealand, +24 more

See more direct flights

Nonstop returns

Chicago to Boston Logan Intl

Monday

ANA, Air New Zealand, Alaska Airlines, +21 more

ANA, Air New Zealand, +22 more

Tuesday

ANA, Air New Zealand, Alaska Airlines, +20 more

ANA, Air New Zealand, +21 more

Wednesday

ANA, Air New Zealand, Alaska Airlines, +22 more

ANA, Air New Zealand, +23 more

Thursday

ANA, Air New Zealand, Alaska Airlines, +21 more

ANA, Air New Zealand, +22 more

Friday

ANA, Air New Zealand, Alaska Airlines, +22 more

ANA, Air New Zealand, +23 more

Saturday

ANA, Air New Zealand, Alaska Airlines, +20 more

ANA, Air New Zealand, +21 more

Sunday

ANA, Air New Zealand, Alaska Airlines, +23 more

ANA, Air New Zealand, +24 more

See more direct flights
See more direct flights

Top 5 airlines serving from Boston to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Boston to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Boston to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
DeltaOverall score based on 10561 reviews
7.4Food
8.2Boarding
7.9Comfort
8.0Entertainment
8.6Crew
Airline reviews

Everything went smoothly. I didn’t like that when I booked in the main cabin my wife and I weren’t seated together. One would think when booking on an option that allows picking your seat. They would put you and your travel partner together. Had to call to get it sorted. They did fix.

8.0 ExcellentEric, May 2024BOS - CUN
Read more about Delta reviews

Everything went smoothly. I didn’t like that when I booked in the main cabin my wife and I weren’t seated together. One would think when booking on an option that allows picking your seat. They would put you and your travel partner together. Had to call to get it sorted. They did fix.

They did a fine job. Can't wait to use Delta in the future.

I usually have a positive experience with Delta. Complimentary upgrades are always nice!

Seats in first class on the E175 recline too far back. I was in 2A, and the man in 1A fully reclined almost the entire flight. It took 6-7 inches of space away from me and made it very difficult to work on my laptop.

Mario was great. Made a night flight on a small aircraft pleasant and memorable.

Crew were exceptional. Plane was quiet and quite empty, so I had a row to sleep across.

The seat could use more support or cushion. I'm in my 50's and have back issues so the seats are a bit hard for longer flights.

The plane was in bad condition. We were taxied for mode than an hour because a light panel had feel off. The bathroom in first class had broken panels as well. Overall poor aircraft maintenance

My only real complaint was how much turbulence there was-and that probably can't be avoided. I felt really sick getting off the plane. But boarding was super easy, the flight attendants were friendly, the bathroom was clean. Everything else about the flight was perfectly fine. Thanks!

Caroline (Supervisor) was great! Salute to the employees like her!

I had back trouble prior to my flight and everyone was great about helping me.

My tv was broken on the flight which is disappointing when you pay for a seat and expect a service

Always delays from Boston to Salt lake but this time was very long. Don’t understand while they board the passengers and then make them sit in the plane

Service for food to our seat was a bit slow. Snack choices were just pretzels or baked chips. My seat cushion was not attached. Other than Barbie, video choice were not very good or current.

After we landed, we were held on the plane for 30 minutes. There was no one at the gate once we landed and we forced to sit on a plan that had already over an hour delayed.

almost 4 hour delay as they over booked and had to wait for 8-10 volunteers to agree to travel next day.

Old plane. No outlets for laptop or phone. Seats worn out. Area around seat dirty.

I loved the flight and the crew. It was comfortable and smooth.

The crew was openly hostile and condescending to the customers. They spent the majority of that time in the rear talking and seemed really agitated when people asked questions. I heard five different people told that the information they requested was in the handout or safety brief.

ticketing issues caused many customers to have to go back to check in after waiting in security, then go through security line again.

No lounge access with “United First” ticket. False alarm about late flight, jeopardizing connection. Wrong meal. Loose power socket would not hold plug, could not charge device. In-flight access to text messaging did not work. Toilet seat on plane would not stay up.

Our original business class flight was cancelled so we not only downgraded but we were also spread out across the plane not sitting together in separate middle seats. My poor kids were scared and couldn’t see me on the flight and the crew wasn’t sensitive to the situation and what the airlines did to us. Very dissatisfied with United airlines.

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

The flight was delayed instead of leaving at 11 it left at 12.20

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

Good movies, iffy pay WiFi, food ok- on time though and that was great!

Awful…flight was delayed more than 12hrs, missed all connections to Fort Wayne, IN, had to get flight to another city 2 hours from my destination, flight was again delayed by 40 mins because they did not have enough fuel, again missed a connection, finally arrived in Indiana at 11pm…but before my 2 hour drive home, ay, no Five That Our Luggage Never Made On The plane and Still In Chicago

Boarding was friendly and quick. While the plane model was older with no live tv, the entertainment was full of movies and tv shows. All food was available. Pilots were very communicative with status of the flight. Flight landed on time.

The flight and crew were fine. The entertainment- the sound was so bad through the headphones I could barely understand it and it was a show I had seen before. The food might have been fine but having to have an account with united in order to access the app in order to pay for the food was rage inducing. I had entered my credit card info at home and logged in as guest but that wouldn’t allow the “wallet” tab to open in the app. And then the wifi was so bad that it took about 45 minutes to fully log in and get all the info working at which time I missed the food. You shouldn’t have to give your address, email and phone number in order to get a hamburger.

The CX617 from HK to BKK was delayed more than 1.5 hours.

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

Those seats were way too narrow. I had the middle seat, one person was a very skinny person and we still couldn’t avoid touching each other anytime one of us moved. The other person was larger and we were basically sitting in each others lap the entire flight. There was zero entertainment. The flight was long enough to justify tvs, but no. Gotta sit there in your infant seat and twiddle your thumbs.

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

Average - flew with Jet Blue internal and it was far more comfortable and better food and entertainment. Notable difference

The flight got canceled due to mechanical issues, and he to be rebooked and missed my appointments for that day

The flight was scheduled to depart DCA at 12:30 pm but was delayed twice on the ground so that we were finally scheduled to depart at around 4:00 pm. Once we boarded, it was announced that takeoff would be delayed again to fix a hydraulic problem which delayed our eventual takeoff until around 5:00 pm. Once we departed, it was a smooth flight back to ORD. We did not get any explanation about what caused the original significant delay. In my experience, this happens frequently with AA.

The only problem experienced was a ground stop in Chicago due to weather. But the crew handled everything professionally. They prioritized rebooking those passengers who had connecting flights and then deplaning the other passengers. When the hold was lifted, they efficiently re-boarded all the passengers so that we could depart before our departure limit expired.

Our second leg to Jackson WY was unable to land due to weather. We were flown back to Dallas after stopping in SLC. We were given hotel rooms and vouchers. We were told that we would be back on the same plane in the morning. Instead we were given a different flight with different seats. Not a good experience. No one knew what was going on.

Crew was nice, explained emergency protocol very well. Flight took off and arrived on time. Pilot explained the small delay that occurred with docking and providing updates. I would definitely fly spirit again.

The seat are terrible. Don’t even think of sleeping on a Spirit flight. The kids that run the plane aka flight attendants are pretty rude and straight forward. They get the job done but without class.

I had a death in my family and booked my flight on Spirit. My flight was cancelled the morning of my flight, no explanation, no help to rebook, nobody to talk to. The next available flight was 2days later !!!! Terrible airline, will NEVER fly with them again!

They took a horrible route with a lot of turbulence and I eneded up getting sick. Even if the flight takes longer. Don't put people life at risk just to get to the airport on time.

Every thing was fine ,low price,easy on time ,clean, good staff, really no issues

Had to board plan 2x due to lack of security check after 1st boarding

Miserable. The crew was rude, the flight was delayed 5 hours for mechanical reasons and then “weather” even though other planes were leaving.

They kept Changing the flight times. It was delayed several times and at one point it was supposed to depart at 3.40am! At which point we ended up staying overnight and booked long a separate United flight for early morning departure. The spirit flight then got moved up and left at 1.30 in the morning when it was supposed to leave at 9.40pm the night before.

Flight was delayed...not horribly late. Just before push back engine shut down for a quick replacement item that took about five minutes. After that, everything was smooth and the pilot was able to make up time in the air so that our arrival time was not too far off the original anticipated arrival time.

The flight was delayed almost two hours on the front end, and an hour on the backend once we landed and waited for a gate to open up. We were told to remain in our seats during that whole delay and I had to go to the bathroom badly. I was unable to hold it and was forced to urinate in my pants while in my seat. I then had to sit in it until we finally deboarded and I was able to change my clothes.

Book cheap flights from Boston to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Boston to Chicago found on KAYAK in the last 72 hours.
6/5Wed
1 stopSpirit Airlines
8h 44mBOS-ORD
$26
8/21Wed
nonstopSpirit Airlines
2h 33mBOS-ORD
$30
6/16Sun
nonstopJetBlue
2h 54mBOS-ORD
$58
6/25Tue
1 stopJetBlue
5h 36mBOS-ORD
$67
7/17Wed
nonstopAmerican Airlines
2h 56mBOS-ORD
$69
6/15Sat
nonstopAmerican Airlines
2h 55mBOS-ORD
$88
7/14Sun
nonstopUnited Airlines
2h 46mBOS-ORD
$89
7/12Fri
nonstopUnited Airlines
2h 50mBOS-ORD
$122
6/14Fri
nonstopDelta
2h 57mBOS-ORD
$124
5/30Thu
nonstopDelta
2h 55mBOS-ORD
$134

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Last minute flights from Boston to Chicago

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Boston to Chicago that are departing in the next 10 days.
5/28Tue
multi-stopSpirit Airlines
24h 15mBOS-ORD
6/4Tue
multi-stopSpirit Airlines
27h 20mORD-BOS
$160
5/26Sun
multi-stopFrontier
8h 13mBOS-MDW
6/3Mon
multi-stopFrontier
8h 27mMDW-BOS
$178
5/28Tue
nonstopAmerican Airlines
2h 57mBOS-ORD
5/31Fri
nonstopAmerican Airlines
2h 17mORD-BOS
$197
5/28Tue
nonstopJetBlue
2h 55mBOS-ORD
6/1Sat
multi-stopJetBlue
4h 34mORD-BOS
$200
5/28Tue
nonstopAmerican Airlines
2h 57mBOS-ORD
5/31Fri
multi-stopAmerican Airlines
4h 40mORD-BOS
$225
5/28Tue
multi-stopJetBlue
7h 37mBOS-ORD
6/4Tue
nonstopJetBlue
2h 29mORD-BOS
$241
5/28Tue
nonstopUnited Airlines
2h 52mBOS-ORD
6/4Tue
nonstopUnited Airlines
2h 20mORD-BOS
$247
5/25Sat
multi-stopDelta
4h 55mBOS-ORD
8/17Sat
nonstopDelta
2h 12mORD-BOS
$257
5/28Tue
nonstopDelta
2h 54mBOS-ORD
6/1Sat
nonstopDelta
2h 29mORD-BOS
$267
5/28Tue
multi-stopUnited Airlines
5h 30mBOS-ORD
5/30Thu
nonstopUnited Airlines
2h 31mORD-BOS
$272

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Boston - Chicago Flights

Departure:

Boston (BOS)United States

Return flight deals:

Chicago - Boston

Cabin classes:

$554
$467
$256
$140

Compare transportation modes for Boston to Chicago

Average priceAverage duration
Flights$1,1982h 51m
Trains$27922h 17m
Buses$20930h 00m