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BOS - CHI

$74 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 11/25. 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.
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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.
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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
6:00 am - 5:41 pmBOS-ORD
12h 41m1 stop
9:55 pm - 8:49 amORD-BOS
9h 54m1 stop
$108Frontier
Find Deal
Sat, Nov 16 - Mon, Nov 18
12:11 pm - 6:41 pmBOS-ORD
7h 30m1 stop
4:38 pm - 7:57 pmORD-BOS
2h 19mnonstop
$109Spirit Airlines
Find Deal
Tue, Nov 12 - Mon, Nov 18
11:05 am - 1:03 pmBOS-ORD
2h 58mnonstop
6:30 am - 10:00 amORD-BOS
2h 30mnonstop
$117Delta
Find Deal
Thu, Dec 5 - Thu, Dec 12
6:00 am - 8:06 amBOS-ORD
3h 06mnonstop
9:10 am - 12:40 pmORD-BOS
2h 30mnonstop
$120JetBlue
Find Deal
Fri, Dec 13 - Thu, Jan 9
6:00 am - 8:06 amBOS-ORD
3h 06mnonstop
10:14 am - 3:43 pmORD-BOS
4h 29m1 stop
$121JetBlue
Find Deal
Mon, Dec 9 - Mon, Dec 9
3:45 pm - 5:46 pmBOS-ORD
3h 01mnonstop
6:40 am - 10:00 amORD-BOS
2h 20mnonstop
$130Delta
Find Deal
Wed, Nov 13 - Sun, Nov 17
5:15 am - 7:17 amBOS-ORD
3h 02mnonstop
7:00 am - 10:19 amORD-BOS
2h 19mnonstop
$151American Airlines
Find Deal
Fri, Nov 22 - Sun, Nov 24
6:00 am - 7:56 amBOS-ORD
2h 56mnonstop
1:55 pm - 5:16 pmORD-BOS
2h 21mnonstop
$161United Airlines
Find Deal
Wed, Nov 6 - Thu, Nov 7
6:00 am - 7:56 amBOS-ORD
2h 56mnonstop
7:22 am - 10:41 amORD-BOS
2h 19mnonstop
$162United Airlines
Find Deal
Thu, Nov 14 - Sun, Nov 17
5:15 am - 7:17 amBOS-ORD
3h 02mnonstop
7:00 am - 1:33 pmORD-BOS
5h 33m1 stop
$187American Airlines
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Wed, Dec 4 - Sun, Dec 8
11:35 am - 9:59 pmBOS-MDW
11h 24m1 stop
$74Frontier
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Mon, Nov 25
12:59 pm - 10:47 pmBOS-ORD
10h 48m1 stop
$74Frontier
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Wed, Dec 18
11:00 am - 1:08 pmBOS-ORD
3h 08mnonstop
$79Delta
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Fri, Jan 10
6:00 am - 8:06 amBOS-ORD
3h 06mnonstop
$81JetBlue
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Wed, Nov 6
5:45 am - 9:34 amBOS-ORD
4h 49m1 stop
$88United Airlines
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Sun, Dec 8
9:00 am - 11:03 amBOS-ORD
3h 03mnonstop
$100Delta
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Fri, Jan 3
7:30 am - 1:15 pmBOS-ORD
6h 45m1 stop
$109United Airlines
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Thu, Jan 2
6:00 am - 8:06 amBOS-ORD
3h 06mnonstop
$124JetBlue
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Thu, Nov 7
5:42 pm - 7:45 pmBOS-ORD
3h 03mnonstop
$134American Airlines
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Mon, Dec 30
5:00 am - 7:04 amBOS-ORD
3h 04mnonstop
$168American Airlines
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Mon, Dec 23
10:50 am - 6:24 pmBOS-ORD
8h 34m1 stop
2:27 pm - 12:29 amORD-BOS
9h 02m1 stop
$100Frontier
Find Deal
Sat, Nov 2 - Wed, Nov 6
10:50 am - 6:24 pmBOS-ORD
8h 34m1 stop
7:05 pm - 12:31 amORD-BOS
4h 26m1 stop
$103Frontier
Find Deal
Sat, Nov 2 - Thu, Nov 7
10:50 am - 6:24 pmBOS-ORD
8h 34m1 stop
4:38 pm - 7:57 pmORD-BOS
2h 19mnonstop
Sat, Nov 2 - Fri, Nov 8
6:00 am - 8:06 amBOS-ORD
3h 06mnonstop
9:56 am - 1:14 pmORD-BOS
2h 18mnonstop
$161JetBlue
Find Deal
Tue, Nov 5 - Sat, Nov 9
8:59 am - 10:50 amBOS-ORD
2h 51mnonstop
6:23 am - 9:47 amORD-BOS
2h 24mnonstop
$169Delta
Find Deal
Tue, Nov 5 - Sun, Nov 10
5:01 am - 9:03 amBOS-ORD
5h 02m1 stop
9:56 am - 1:14 pmORD-BOS
2h 18mnonstop
$170JetBlue
Find Deal
Tue, Nov 5 - Sat, Nov 9
5:20 am - 9:09 amBOS-ORD
4h 49m1 stop
6:23 am - 9:47 amORD-BOS
2h 24mnonstop
$247Delta
Find Deal
Sun, Nov 3 - Thu, Nov 7
6:28 pm - 8:24 pmBOS-ORD
2h 56mnonstop
1:55 pm - 5:16 pmORD-BOS
2h 21mnonstop
$279United Airlines
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Fri, Nov 1 - Sat, Nov 9
6:55 pm - 11:00 pmBOS-ORD
5h 05m1 stop
6:25 pm - 9:50 pmORD-BOS
2h 25mnonstop
$289United Airlines
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Fri, Nov 1 - Sat, Nov 9
3:50 pm - 7:33 pmBOS-ORD
4h 43m1 stop
8:20 pm - 11:51 pmORD-BOS
2h 31mnonstop
$309American Airlines
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Fri, Nov 1 - Sat, Nov 9
7:40 am - 9:50 amBOS-ORD
3h 10mnonstop
4:38 pm - 7:57 pmORD-BOS
2h 19mnonstop
$75Spirit Airlines
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Sun, Nov 17 - Mon, Nov 18
7:40 am - 9:50 amBOS-ORD
3h 10mnonstop
7:50 pm - 11:08 pmORD-BOS
2h 18mnonstop
$77Spirit Airlines
Find Deal
Tue, Nov 12 - Thu, Nov 14
7:50 pm - 9:51 pmBOS-ORD
3h 01mnonstop
12:40 pm - 4:01 pmORD-BOS
2h 21mnonstop
$117Delta
Find Deal
Wed, Nov 13 - Sat, Nov 16
6:00 am - 8:06 amBOS-ORD
3h 06mnonstop
9:10 am - 12:40 pmORD-BOS
2h 30mnonstop
$120JetBlue
Find Deal
Fri, Dec 13 - Wed, Jan 8
6:00 am - 8:06 amBOS-ORD
3h 06mnonstop
8:51 am - 12:13 pmORD-BOS
2h 22mnonstop
$123JetBlue
Find Deal
Fri, Dec 6 - Sun, Dec 8
3:45 pm - 5:46 pmBOS-ORD
3h 01mnonstop
6:40 am - 10:00 amORD-BOS
2h 20mnonstop
$130Delta
Find Deal
Wed, Nov 13 - Sun, Nov 17
5:15 am - 7:17 amBOS-ORD
3h 02mnonstop
7:00 am - 10:19 amORD-BOS
2h 19mnonstop
$151American Airlines
Find Deal
Fri, Nov 22 - Sun, Nov 24
6:00 am - 7:56 amBOS-ORD
2h 56mnonstop
7:22 am - 10:41 amORD-BOS
2h 19mnonstop
$156United Airlines
Find Deal
Fri, Nov 22 - Sun, Nov 24
6:45 am - 8:49 amBOS-ORD
3h 04mnonstop
8:30 pm - 12:15 amORD-BOS
2h 45mnonstop
$158American Airlines
Find Deal
Thu, Jan 2 - Sun, Jan 5
6:00 am - 7:56 amBOS-ORD
2h 56mnonstop
7:22 am - 10:41 amORD-BOS
2h 19mnonstop
$162United Airlines
Find Deal
Thu, Nov 14 - Sun, Nov 17
12:50 pm - 10:12 amBoston South Station-
Chicago Union
22h 22mnonstop
9:30 pm - 8:32 pmChicago Union-
Boston South Station
22h 02mnonstop
$264Amtrak
Find Deal
Sat, Nov 16 - Tue, Nov 19
7:45 pm - 10:40 pmBoston South Station-
Chicago Dan Ryan Greyhound
27h 55mnonstop
2:25 pm - 6:35 pmChicago Dan Ryan Greyhound-
Boston South Station
27h 10mnonstop
$309Greyhound
Find Deal
Fri, Nov 29 - Tue, Dec 3
7:45 pm - 10:40 pmBoston South Station-
Chicago Dan Ryan Greyhound
27h 55mnonstop
2:25 pm - 6:35 pmChicago Dan Ryan Greyhound-
Boston South Station
27h 10mnonstop
$309Greyhound
Find Deal
Fri, Nov 29 - Tue, Dec 3
7:45 pm - 10:40 pmBoston South Station-
Chicago Dan Ryan Greyhound
27h 55mnonstop
2:25 pm - 6:35 pmChicago Dan Ryan Greyhound-
Boston South Station
27h 10mnonstop
$310Greyhound
Find Deal
Fri, Nov 29 - Tue, Dec 3
7:45 pm - 10:40 pmBoston South Station-
Chicago Dan Ryan Greyhound
27h 55mnonstop
2:25 pm - 6:35 pmChicago Dan Ryan Greyhound-
Boston South Station
27h 10mnonstop
$310Greyhound
Find Deal
Fri, Nov 29 - Tue, Dec 3
5:15 pm - 8:05 pmBoston South Station-
Chicago Downtown Greyhound Station
27h 50mnonstop
10:30 pm - 12:25 pmChicago Downtown Greyhound Station-
Boston South Station
36h 55mnonstop
$433FlixBus, Greyhound
Find Deal
Thu, Nov 7 - Sat, Nov 30
8:50 am - 2:40 pmBoston South Station-
Chicago Union
30h 50mnonstop
10:00 pm - 12:25 pmChicago Union-
Boston South Station
37h 25mnonstop
$449Greyhound
Find Deal
Thu, Nov 7 - Sat, Nov 30
5:15 pm - 8:05 pmBoston South Station-
Chicago Downtown Greyhound Station
27h 50mnonstop
10:30 pm - 12:25 pmChicago Downtown Greyhound Station-
Boston South Station
36h 55mnonstop
$451FlixBus, Greyhound
Find Deal
Fri, Nov 29 - Tue, Dec 3
5:15 pm - 8:05 pmBoston South Station-
Chicago Downtown Greyhound Station
27h 50mnonstop
10:30 pm - 12:25 pmChicago Downtown Greyhound Station-
Boston South Station
36h 55mnonstop
$451FlixBus, Greyhound
Find Deal
Fri, Nov 29 - Tue, Dec 3
5:15 pm - 8:05 pmBoston South Station-
Chicago Downtown Greyhound Station
27h 50mnonstop
10:30 pm - 12:25 pmChicago Downtown Greyhound Station-
Boston South Station
36h 55mnonstop
$451FlixBus, Greyhound
Find Deal
Fri, Nov 29 - Tue, Dec 3

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 $78 and was between Boston and Chicago O'Hare Intl Airport. On average, the best prices are found if you fly this route. The average price for a return flight for this route is $116.

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 Sundays if you are looking for the best rates. For your return to Boston, you’ll find the best rates on Wednesdays and the most expensive ones on Sundays.

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 September, where tickets cost $184 on average. On the other hand, the most expensive months are April and May, where the average cost of tickets is $299 and $293 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 1 week before departure. For the absolute cheapest price, our data suggests you should book 168 days before departure.
 AI-powered savings tips

How to save more on a Boston to Chicago flight

When planning a flight from Boston to Chicago, it's important to consider a few factors to ensure you're getting the best deal. Generally, Tuesdays are the cheapest day of the week to fly, while January tends to be the cheapest month.

Day Selection: Choose to fly on a Tuesday for the best rates.

Advance Booking: Book your flight at least 23 days in advance to secure the best prices.

Airline Choice: Spirit Airlines typically offers the cheapest fares for this route.

Route Selection: The route from Boston Logan Intl to Chicago O'Hare Intl is usually the cheapest.

Flight Type: Direct flights are significantly more expensive, consider flights with layovers to save money.

This feature is powered by ChatGPT: an OpenAI-developed artificial intelligence model trained with KAYAK proprietary data and third-party data not verified by KAYAK. 


Good to know

Low season

January

High season

October

Cheapest flight

$74
Best time to beat the crowds with an average 24% drop in price.
Most popular time to fly with an average 5% increase in price.
Flight from Boston to Chicago Midway 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 recycled plastics and pack light for the trip.

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

    If you’ll be driving to the airport, you’ll be happy to know that Boston Logan International Airport (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)?

    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 (ORD)?

    Yes, Chicago O’Hare International Airport (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 also at Gate M8​, Gate M20​, Gate M32 and Gate M37 in Terminal 5. There are also others at Multi-Modal Facility on Level 1, North and South Side.

  • If I want to use mass transit to get to Boston Logan International Airport (BOS), 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 (BOS)?

    The pet relief areas at Boston Logan International Airport (BOS) 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 (ORD), where is the best place to meet my ride?

    For most requests, you'll meet your rideshare driver on the Departures level of Terminal 2. 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 (ORD)?

    The airport offers a complimentary shuttle to the airport's Multi-Modal Facility, where all on-site car rental companies are located. Travelers can find 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 $74 for a one-way ticket and $108 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, Delta, and JetBlue 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, Southwest or Delta?

    The two airlines most popular with KAYAK users for flights from Boston to Chicago are Southwest and Delta. With an average price for the route of $212 and an overall rating of 8.1, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $262 and an overall rating of 8.0.

  • 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

KAYAK’s 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 $165 or less one-way and $260 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 (LGA).
  • 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 modes of transportation.
  • Passengers flying to Chicago O’Hare International Airport (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.
  • If you need cash before flying out from Boston Logan International Airport (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.
  • Travelers with kids will be glad to learn that Boston Logan International Airport (BOS) has Kidports where their kids can let off steam 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.
  • Before your flight from Boston to Chicago, be sure to get a taste of some excellent seafood at Legal Sea Foods. 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 (BOS), 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 Classique Hair Salon? Located in Terminal C near Gare C-25 at Boston Logan International Airport, Classique Hair Salon 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 Boston Logan Intl Airport to Chicago, which days they fly and book direct flights.

Nonstop departures

Boston Logan Intl to Chicago

Monday

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

ANA, Air New Zealand, +22 more

Tuesday

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

ANA, Air New Zealand, +23 more

Wednesday

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

ANA, Air New Zealand, +21 more

Thursday

ANA, Air New Zealand, Alaska Airlines, +24 more

ANA, Air New Zealand, +25 more

Friday

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

ANA, Air New Zealand, +24 more

Saturday

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

ANA, Air New Zealand, +23 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, +21 more

ANA, Air New Zealand, +22 more

Wednesday

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

ANA, Air New Zealand, +22 more

Thursday

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

ANA, Air New Zealand, +24 more

Friday

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

ANA, Air New Zealand, +23 more

Saturday

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

ANA, Air New Zealand, +23 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 8835 reviews
7.9Comfort
7.3Food
8.2Boarding
8.5Crew
7.9Entertainment
Airline reviews

I upgraded to first class only to find out that I still had no access to the sky lounge without a sky miles card or AmEx (something that should be emphasized outside of the fine print!) Also, no food or drink service provided during the flight, so I basically paid 4x more just for “free” checked baggage and a bigger seat. Not worth it.

2.0 MediocreEric, Oct 2024SLC - ABQ
Read more Delta reviews

I upgraded to first class only to find out that I still had no access to the sky lounge without a sky miles card or AmEx (something that should be emphasized outside of the fine print!) Also, no food or drink service provided during the flight, so I basically paid 4x more just for “free” checked baggage and a bigger seat. Not worth it.

Delta was really good about being transparent with why we were delayed it’s just that’s the plane was really old and outdated and a lot of the comfort and amenities we know Delta to have did not shine through

Bottom seat cushion is almost non existent. Very uncomfortable seat.

Delta was great the entertainment was outdated. Screen was very small and didn’t work.

Flight did not have seat back entertainment and the wifi was iffy.

Pretty standard flight. Delta has a good selection of movies.

The WiFi has been awful on my last few Delta Air Lines flights.

The seats are uncomfortable, feels like a small seat pad on plywood.

The seats are uncomfortable and there was no power to recharge a phone.

Flight heavily delayed. No food available despite purchasing an upgrade. No in cabin service.

Smooth boarding and friendly crew. Unfortunately as soon as we boarded the unit that provides air circulation failed. The pilot informed us and requested maintenance technicians to check it out. The plane became uncomfortably warm without any fresh air coming in. Plus the repair delayed our departure. I am glad the maintenance crew were able to fix the problem. I also was without use of my tv monitor for the first 1/3rd of the trip.

Communication with the customer and stay is important. Staff off with a minor inconvenience but it worked out of course. Also this was a very old Mint Class plane. They snuck this one in on us. The updated aircraft are much better.

The flight itself was fine, but the boarding process was extremely frustrating. There is no one scanning boarding passes - passengers just scan themselves and enter the jetway. By the time my husband and I got on the plane and were halfway to our seats they determined there were too many bags on the plane and everything at that point needed to be checked. This created a lot of unnecessary chaos. They should have alerted people before getting on the plane that they would need to start checking bags instead of waiting until people were already on the plane.

The best flight I’ve had in a while. The plane was like 25% capacity, if that. Smoothest boarding and deplaning process I’ve ever experienced. Wish all flights were this smooth.

Did not enjoy this flight at all. All of my coworkers flew delta and I chose JetBlue because I really value how simple the WiFi and entertainment is and this flight I didn’t get either. Crew staff was unsympathetic to my system not working, everyone I asked for help with was extremely bothered by my request for help.

Little snafu at boarding. Staff communicated with gate poorly. Flight attendant was rude making disembark early. This was an older mint class. Needs an overhaul for sure. Food was good. The male flight attendant was really nice.

My encounter with the entertainment services provided on board was moderate; the functionality of the Wi-Fi connection was either sluggish or nonoperational, while the display screens were antiquated and suffered from poor visibility. On the positive side, the cabin exuded a sense of expansiveness, and the crew exhibited amiable and accommodating behavior throughout the journey.

Everything was great except for some reason crew and ground crew could not figure out how to deal with an electric wheelchair and it delayed us 20-30mins. Was pretty frustrating for passengers and the captain.

Like the space, did not like the snack options, there was no power outlet in seats, no entertainment, no flyfi.

Traveling with JetBlue from NYC was convenient as accessing JFK airport was straightforward via the LIRR to the AirTrain. Maneuvering through the terminal was hassle-free, which was a pleasant start to the journey. However, the flight experience itself left much to be desired. The seating arrangement was notably uncomfortable; despite securing a window seat, space felt cramped. This was exacerbated by the middle seat passenger encroaching on my area, which made the flight less enjoyable. Additionally, while the in-flight entertainment system initially seemed like a reprieve, the sound outlet on my seat was inoperable. This issue turned what could have been a manageable three-hour flight into a rather tedious ordeal, as I was unable to use the entertainment system effectively. While JetBlue provided a smooth process in terms of airport logistics, the on-board experience highlighted areas in need of improvement, particularly in terms of comfort and entertainment system maintenance.

Pleasant service from the crew. Arrived early. Efficient boarding and deplaning. Great job!

Everything was very good. Was able to change a make run flight leaving on direct earlier in the app -seamless!!! Well done

Being stick waiting for gate at ORD cause me to almost miss my connecting flight…being deaf United made no no effort to keep me updated as I couldn’t hear the PA

As usual, United scheduling is completely misleading. A 54-minute layover at O’Hare is too short to make a lot of connections, especially since the flight landed “on time” but had to wait on the taxiway 15 minutes for a gate to open up. Then it takes another 10 minutes to exit the plane before one can run to another concourse to catch a connecting flight.

The seats on the aircraft are like sitting in a rock. During the boarding process they recognize Active Duty Military, why don’t they recognize Retired Military. I’ve always preferred Delta, this flight confirmed why I still prefer Delta.

when you can say you don't remember being at any point upset during a flight, the airline is winning .

The staff was very friendly. The seats seemed quite small. Overall the flight was pleasant.

It was literally one of the worst travel experiences ever. My flight got delayed by over an hour and there was no communication of this from the gate staff. I realized it by checking the screen periodically. Once on board the flight attendants continued to serve alcohol to a man who was clearly already drunk and that was making a bunch of commotion. Never again will I fly United!

Charging and entertainment didn't work. The meal was horrible. They only came by with the drink cart one time for the 8 hour flight. They did come by with water a couple times.

Exceptional, I’d like to specifically recognize Robert for his outstanding customer service. He is professional, pleasant, and personable.

Airplane was cold. Flight attendants were rude. Phone charger did not work. No food available.

3hour delay In the last 3 months i had 3 flights and 2 of these had a more than 2:40 hrs delayed

My initial flight to ORD was extended without reason. We circled the airport a few time and then drove on the ground for at least 20 minutes. These kinds of delays are annoying but somewhat expected… it would be nice if the crew would make an announcement to give updates on how long we could expect to be delayed.

The flight was uneventful. What was a problem was I was delayed getting home one entire day because the flight from Sacramento was delayed. That made getting to my connecting flight impossible. I had to stay another night at the hotel and incur that expense as a result.

AA is fabulous. However , Iberia cancelled our Boston - Barcelona flight the morning of the flight - 9/16/24. This was almost a week ago and we have still heard nothing from Iberia/Vueling. Found out from a kayak email that morning that the flight was cancelled. Iberia Customer service reps wouldn’t help us and said to call Vueling. No one answers phone at Vueling. Terrible wild goose chase on DAY OF TRAVEL. AA came to our rescue.

Boston ticket agent Cheryl Porter is WONDERFUL. Our Iberia flight to Barcelona was cancelled the morning we were scheduled to leave and Cheryl was our super hero - she found us seats on a flight to London and on to Barcelona. Truly a “can-do” attitude which we appreciated so much after the Iberia ticket agents told us there was “absolutely nothing they could do”. (As did the customer service agents at Iberia’s call center) Ms Porter is truly a wonderful person who genuinely cares about travelers!

The foot ottoman cushion was missing on my business class seat.. the hydraulics is on its last leg & seat cushions do not have support or paddling. Heavily dented by butts

This flight was fine but had no time to breathe as the connection was late from Sea to ORD.. Super stressful. If we checked bags, the trip would have been very distressed.

Seats were very uncomfortable. I paid extra for a seat with more leg room, the seat was no different than a seat at the back of the plane. Flight attendant was rude.

the food choice of packaged chips and popcorn was utterly ridiculous for first class

The flight landed with a delay and we had to wait almost an hour to be off boarded. So typical of spirit.

The gate employees and the flight crew were friendly and professional. Afterboarding we waited 20 minutes for another flight; a complimentary beverage would have ben appreciated for the inconvenience.

Spirit literally broke parts of two of our suitcases and call it “normal wear and tear.” Not worth the low price if we have to replace bags.

You get what you pay for, but those tickets weren't cheap, so I expected better, but Spirit is just one of those airlines.

The worse experience ever from flight delays customer service and professionalism.

Terrible they delayed our flight then when we got on they had to fix the plane then finally we left hours later and when we got there since they had screwed up everything else we had to wait for a walkway so we had to sit on the plane and they turned off the AC and it was fuckin hot

Cancelled the return flight moments before boarding, horrible customer service in assisting with any rebooking. Never again will I fly Spirit.

Flight got diwngraded last minute and left us stranded. I was told I’ll be given credit for my luggage and seat upgrades but haven’t got anything yet

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.

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.
11/25Mon
1 stopFrontier
11h 24mBOS-MDW
$74
12/18Wed
1 stopFrontier
10h 48mBOS-ORD
$74
1/10Fri
nonstopDelta
3h 08mBOS-ORD
$79
11/6Wed
nonstopJetBlue
3h 06mBOS-ORD
$81
12/8Sun
1 stopUnited Airlines
4h 49mBOS-ORD
$88
1/3Fri
nonstopDelta
3h 03mBOS-ORD
$100
1/2Thu
1 stopUnited Airlines
6h 45mBOS-ORD
$109
11/7Thu
nonstopJetBlue
3h 06mBOS-ORD
$124
12/30Mon
nonstopAmerican Airlines
3h 03mBOS-ORD
$134
12/23Mon
nonstopAmerican Airlines
3h 04mBOS-ORD
$168

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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.
11/2Sat
multi-stopFrontier
8h 34mBOS-ORD
11/6Wed
multi-stopFrontier
9h 02mORD-BOS
$100
11/2Sat
multi-stopFrontier
8h 34mBOS-ORD
11/7Thu
multi-stopFrontier
4h 26mORD-BOS
$103
11/2Sat
multi-stop
8h 34mBOS-ORD
11/8Fri
nonstop
2h 19mORD-BOS
$126
11/5Tue
nonstopJetBlue
3h 06mBOS-ORD
11/9Sat
nonstopJetBlue
2h 18mORD-BOS
$161
11/5Tue
nonstopDelta
2h 51mBOS-ORD
11/10Sun
nonstopDelta
2h 24mORD-BOS
$169
11/5Tue
multi-stopJetBlue
5h 02mBOS-ORD
11/9Sat
nonstopJetBlue
2h 18mORD-BOS
$170
11/3Sun
multi-stopDelta
4h 49mBOS-ORD
11/7Thu
nonstopDelta
2h 24mORD-BOS
$247
11/1Fri
nonstopUnited Airlines
2h 56mBOS-ORD
11/9Sat
nonstopUnited Airlines
2h 21mORD-BOS
$279
11/1Fri
multi-stopUnited Airlines
5h 05mBOS-ORD
11/9Sat
nonstopUnited Airlines
2h 25mORD-BOS
$289
11/1Fri
multi-stopAmerican Airlines
4h 43mBOS-ORD
11/9Sat
nonstopAmerican Airlines
2h 31mORD-BOS
$309

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Everything you need to know for your flight from Boston to Chicago

Information on your arrival and departure airports

Compare transportation modes for Boston to Chicago

Average priceAverage duration
Flights$5782h 45m
Trains$26422h 20m
Buses$42931h 10m