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CHI - BOS

$31 Find Cheap Flights from Chicago to Boston

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Boston departing on 11/24. 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 Chicago to Boston.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Boston.
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Cheap Flight Deals from Chicago to Boston (CHI-BOS)

 
These are the cheapest deals for flights from Chicago to Boston 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 Chicago to Boston

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

Recent one-way flight deals from Chicago to Boston

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

Recent last minute flight deals from Chicago to Boston

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

Recent direct flight deals from Chicago to Boston

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

Cheap bus & train deals from Chicago to Boston

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

All round-trip flight deals to Boston

The cheapest plane tickets to Boston found on KAYAK recently.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
8:27 pm - 9:14 amORD-BOS
11h 47m1 stop
5:00 am - 4:06 pmBOS-ORD
12h 06m1 stop
$92Spirit Airlines
Find Deal
Tue, Dec 3 - Tue, Dec 10
7:39 pm - 9:14 amORD-BOS
12h 35m1 stop
12:00 pm - 8:15 pmBOS-ORD
9h 15m1 stop
$94Spirit Airlines
Find Deal
Tue, Dec 3 - Wed, Dec 4
4:40 pm - 8:02 pmORD-BOS
2h 22mnonstop
6:00 am - 8:06 amBOS-ORD
3h 06mnonstop
$157JetBlue
Find Deal
Fri, Dec 6 - Sun, Dec 8
10:14 am - 3:43 pmORD-BOS
4h 29m1 stop
6:00 am - 8:06 amBOS-ORD
3h 06mnonstop
$166JetBlue
Find Deal
Tue, Dec 10 - Sun, Dec 15
7:35 am - 11:03 amORD-BOS
2h 28mnonstop
7:15 am - 9:25 amBOS-ORD
3h 10mnonstop
$178Delta
Find Deal
Sat, Jan 4 - Wed, Jan 8
8:05 am - 11:26 amORD-BOS
2h 21mnonstop
8:45 am - 10:49 amBOS-ORD
3h 04mnonstop
$179American Airlines
Find Deal
Wed, Dec 25 - Wed, Jan 1
7:35 am - 11:03 amORD-BOS
2h 28mnonstop
9:00 am - 11:03 amBOS-ORD
3h 03mnonstop
$189Delta
Find Deal
Tue, Dec 24 - Tue, Dec 31
6:35 pm - 10:04 pmORD-BOS
2h 29mnonstop
8:00 am - 12:18 pmBOS-ORD
5h 18m1 stop
$207American Airlines
Find Deal
Fri, Dec 13 - Sun, Dec 15
9:30 pm - 12:54 amORD-BOS
2h 24mnonstop
6:02 am - 8:05 amBOS-ORD
3h 03mnonstop
$213United Airlines
Find Deal
Sun, Dec 22 - Tue, Dec 31
9:30 pm - 12:54 amORD-BOS
2h 24mnonstop
6:02 am - 8:05 amBOS-ORD
3h 03mnonstop
$235United Airlines
Find Deal
Fri, Dec 20 - Tue, Dec 31
4:45 pm - 8:04 pmORD-BOS
2h 19mnonstop
$31Spirit Airlines
Find Deal
Sun, Nov 24
4:45 pm - 8:04 pmORD-BOS
2h 19mnonstop
$37Spirit Airlines
Find Deal
Sun, Nov 24
2:35 pm - 6:10 pmORD-BOS
2h 35mnonstop
$79Delta
Find Deal
Thu, Jan 9
10:14 am - 6:45 pmORD-BOS
7h 31m1 stop
$88JetBlue
Find Deal
Tue, Dec 10
7:00 am - 10:15 amORD-BOS
2h 15mnonstop
$89JetBlue
Find Deal
Sun, Jan 12
7:35 am - 11:03 amORD-BOS
2h 28mnonstop
$90Delta
Find Deal
Tue, Dec 24
2:00 pm - 5:23 pmORD-BOS
2h 23mnonstop
$114United Airlines
Find Deal
Tue, Jan 7
9:30 pm - 12:54 amORD-BOS
2h 24mnonstop
$115United Airlines
Find Deal
Sat, Dec 21
7:00 am - 10:19 amORD-BOS
2h 19mnonstop
$126American Airlines
Find Deal
Sun, Nov 17
8:19 am - 3:21 pmORD-BOS
6h 02m1 stop
$133American Airlines
Find Deal
Sat, Nov 16
7:05 pm - 12:31 amORD-BOS
4h 26m1 stop
7:40 am - 9:50 amBOS-ORD
3h 10mnonstop
Thu, Nov 14 - Tue, Nov 19
7:05 pm - 12:31 amORD-BOS
4h 26m1 stop
7:40 am - 9:50 amBOS-ORD
3h 10mnonstop
Thu, Nov 14 - Tue, Nov 19
2:27 pm - 12:29 amORD-BOS
9h 02m1 stop
11:35 am - 12:28 amBOS-ORD
13h 53m1 stop
$114Frontier
Find Deal
Wed, Nov 13 - Sat, Nov 23
7:50 pm - 11:08 pmORD-BOS
2h 18mnonstop
7:40 am - 9:50 amBOS-ORD
3h 10mnonstop
$160Spirit Airlines
Find Deal
Thu, Nov 14 - Tue, Nov 19
5:34 pm - 6:36 pmORD-BOS
24h 02m3 stops
12:11 pm - 6:41 pmBOS-ORD
7h 30m1 stop
$170Spirit Airlines
Find Deal
Fri, Nov 15 - Tue, Nov 19
10:35 am - 2:00 pmORD-BOS
2h 25mnonstop
10:45 am - 12:41 pmBOS-ORD
2h 56mnonstop
$247United Airlines
Find Deal
Fri, Nov 15 - Sat, Nov 16
10:25 am - 1:55 pmORD-BOS
2h 30mnonstop
7:25 am - 9:28 amBOS-ORD
3h 03mnonstop
$252Delta
Find Deal
Thu, Nov 14 - Fri, Dec 6
10:30 am - 3:50 pmORD-BOS
4h 20m1 stop
7:45 pm - 9:43 pmBOS-ORD
2h 58mnonstop
$262Delta
Find Deal
Thu, Nov 14 - Fri, Dec 6
8:41 am - 12:03 pmORD-BOS
2h 22mnonstop
6:00 am - 8:06 amBOS-ORD
3h 06mnonstop
$297JetBlue
Find Deal
Wed, Nov 13 - Sun, Nov 17
8:41 am - 12:03 pmORD-BOS
2h 22mnonstop
5:01 am - 9:03 amBOS-ORD
5h 02m1 stop
$306JetBlue
Find Deal
Wed, Nov 13 - Mon, Nov 18
4:45 pm - 8:04 pmORD-BOS
2h 19mnonstop
8:10 am - 10:21 amBOS-ORD
3h 11mnonstop
$104Spirit Airlines
Find Deal
Mon, Nov 25 - Tue, Dec 3
4:45 pm - 8:04 pmORD-BOS
2h 19mnonstop
8:10 am - 10:21 amBOS-ORD
3h 11mnonstop
$111Spirit Airlines
Find Deal
Thu, Nov 21 - Tue, Dec 3
9:10 am - 12:40 pmORD-BOS
2h 30mnonstop
3:50 pm - 5:53 pmBOS-ORD
3h 03mnonstop
$151JetBlue
Find Deal
Sat, Jan 18 - Sat, Jan 18
2:05 pm - 5:34 pmORD-BOS
2h 29mnonstop
7:25 am - 9:28 amBOS-ORD
3h 03mnonstop
$157Delta
Find Deal
Fri, Dec 6 - Tue, Dec 10
4:40 pm - 8:00 pmORD-BOS
2h 20mnonstop
6:00 am - 8:06 amBOS-ORD
3h 06mnonstop
$167JetBlue
Find Deal
Tue, Dec 3 - Thu, Dec 12
1:55 pm - 5:16 pmORD-BOS
2h 21mnonstop
9:30 am - 11:28 amBOS-ORD
2h 58mnonstop
$168United Airlines
Find Deal
Wed, Dec 18 - Tue, Dec 31
8:05 am - 11:26 amORD-BOS
2h 21mnonstop
8:45 am - 10:49 amBOS-ORD
3h 04mnonstop
$179American Airlines
Find Deal
Wed, Dec 25 - Wed, Jan 1
7:35 am - 11:03 amORD-BOS
2h 28mnonstop
9:00 am - 11:03 amBOS-ORD
3h 03mnonstop
$189Delta
Find Deal
Tue, Dec 24 - Tue, Dec 31
9:35 pm - 12:54 amORD-BOS
2h 19mnonstop
12:25 pm - 2:21 pmBOS-ORD
2h 56mnonstop
$195United Airlines
Find Deal
Tue, Nov 26 - Tue, Dec 3
6:55 pm - 10:24 pmORD-BOS
2h 29mnonstop
6:45 am - 8:49 amBOS-ORD
3h 04mnonstop
$208American Airlines
Find Deal
Mon, Nov 25 - Mon, Dec 30
9:30 pm - 8:32 pmChicago Union-
Boston South Station
22h 02mnonstop
12:50 pm - 10:12 amBoston South Station-
Chicago Union
22h 22mnonstop
$264Amtrak
Find Deal
Thu, Dec 5 - Mon, Dec 9
9:30 pm - 8:32 pmChicago Union-
Boston South Station
22h 02mnonstop
12:50 pm - 10:12 amBoston South Station-
Chicago Union
22h 22mnonstop
$264Amtrak
Find Deal
Thu, Dec 5 - Mon, Dec 9
9:30 pm - 8:24 pmChicago Union-
Boston Back Bay
21h 54mnonstop
12:57 pm - 10:12 amBoston Back Bay-
Chicago Union
22h 15mnonstop
$264Amtrak
Find Deal
Thu, Dec 5 - Mon, Dec 9
9:30 pm - 8:24 pmChicago Union-
Boston Back Bay
21h 54mnonstop
12:57 pm - 10:12 amBoston Back Bay-
Chicago Union
22h 15mnonstop
$264Amtrak
Find Deal
Thu, Dec 5 - Mon, Dec 9
9:30 pm - 8:24 pmChicago Union-
Boston Back Bay
21h 54mnonstop
12:57 pm - 10:12 amBoston Back Bay-
Chicago Union
22h 15mnonstop
$291Amtrak
Find Deal
Fri, Dec 6 - Tue, Dec 10
9:30 pm - 8:32 pmChicago Union-
Boston South Station
22h 02mnonstop
12:50 pm - 10:12 amBoston South Station-
Chicago Union
22h 22mnonstop
$291Amtrak
Find Deal
Mon, Dec 2 - Mon, Dec 9
9:30 pm - 8:32 pmChicago Union-
Boston South Station
22h 02mnonstop
12:50 pm - 10:12 amBoston South Station-
Chicago Union
22h 22mnonstop
$291Amtrak
Find Deal
Fri, Dec 6 - Tue, Dec 10
9:30 pm - 8:32 pmChicago Union-
Boston South Station
22h 02mnonstop
12:50 pm - 10:12 amBoston South Station-
Chicago Union
22h 22mnonstop
$291Amtrak
Find Deal
Wed, Dec 4 - Tue, Dec 10
9:30 pm - 8:32 pmChicago Union-
Boston South Station
22h 02mnonstop
12:50 pm - 10:12 amBoston South Station-
Chicago Union
22h 22mnonstop
$291Amtrak
Find Deal
Wed, Dec 4 - Fri, Dec 6
9:30 pm - 8:24 pmChicago Union-
Boston Back Bay
21h 54mnonstop
12:57 pm - 10:12 amBoston Back Bay-
Chicago Union
22h 15mnonstop
$291Amtrak
Find Deal
Wed, Dec 4 - Sun, Dec 8

Flights from Chicago to Boston - Travel Insights & Trends

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

What is the cheapest Chicago to Boston flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for one-way flights from Chicago to Boston.
Our data shows that the cheapest route for a one-way flight from Chicago to Boston cost $62 and was between Chicago Midway Airport and Boston. On average, the best prices are found if you fly this route. The average price for a return flight for this route is $128.

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

The average price of all flights from Chicago to Boston clicked on KAYAK for each day over the last 12 months.
Your flight ticket price will generally be cheaper if you fly to Boston on a Wednesday and more expensive on a Sunday. On your return trip to Chicago, you should consider flying back on a Tuesday, and avoid Sundays for better deals.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Chicago to Boston, 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 Chicago to Boston is September, where tickets cost $191 on average. On the other hand, the most expensive months are April and May, where the average cost of tickets is $298 and $284 respectively.

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

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Chicago to Boston, 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 Chicago to Boston, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 145 days before departure.
 AI-powered savings tips

How to save more on a Chicago to Boston flight

When planning a flight from Chicago to Boston, there are several strategies to consider for saving money. Generally, the cheapest day of the week to fly is Wednesday, and the most affordable month is September.

Booking Advance: Purchase tickets at least 90 days in advance for the best rates.

Airline Choice: Consider flying with Frontier, as it is generally the cheapest airline for this route.

Route Selection: Flights from Chicago Midway (MDW) to Boston Logan (BOS) tend to be the most affordable.

Direct or Layover: Direct flights are significantly more expensive, so 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

$31
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly and prices are also 9% lower on average.
Flight from Chicago O'Hare Airport to Boston

When to book flights from Chicago to Boston

Are your dates flexible? Find out the best times to travel from Chicago to Boston 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 Chicago to Boston

  • How can I get to the Freedom Trail from Boston Logan International Airport (BOS)?

    The distance between the Freedom Trail and Boston Logan International Airport (BOS) is around 3.7 miles, and various transportation options run between the two points. Line 88 bus and the subway provide the best opportunity to travel between the two points, taking about 26min to cover the distance. However, a taxi is a quicker option, taking about 6min to get there.

  • Where are spas located at Boston Logan International Airport (BOS)?

    Travelers arriving in BOS from Chicago while weary can seek some therapy in one of the spas on this property. XpresSpa at Terminal B provides ideal services to help you relax and self-indulge. They include manicures, pedicures, facials, and deep-tissue massages.

  • Where can I withdraw money at Boston Logan International Airport (BOS)?

    If your wallet is depleted and you want to recharge it, you’ll find several ATMs at BOS run by numerous banks and credit unions. These ATMs are located throughout the airport terminals, pre-and post-security. For instance, Bank of America has its ATMs at the Arrivals Level, East End by Taxi Stand, Pre-Security.

  • What family-friendly amenities are at Boston Logan International Airport (BOS)?

    BOS caters to the needs of moms and the littlest family members through the provision of Mamava suites where lactating mothers can pump and breastfeed in privacy. You can locate one of them in Terminal E post-security in the Women's Restroom lobby.

  • Does Logan International Airport have pet relief areas?

    If you are traveling with a pet or service animal, make sure to stop by one of the pet relief areas in Logan International Airport after your flight has landed. There is a designated area conveniently located outside of the Arrivals doors for every terminal, and complimentary waste bags are provided for pet owners.

  • What are good hotels near Logan International Airport?

    The Hilton Boston Logan Airport is a chic, 4-star hotel that is directly connected to Logan International Airport via a skybridge and is less than a 7-minute drive from the Boston Common Park. The Hyatt Regency Boston Harbor is a standard option that is only a mile from the airport and a 5-minute drive from the famous Faneuil Hall.

  • What dining options are there in Chicago Midway International Airport?

    The Go Go White Sox Bar and Grill is located in the Central Market of Chicago Midway International Airport and serves classic American meals, while the Midway Pour House is in Concourse A and is known for having a variety of craft beers. Dunkin’ Donuts and Cafe Espresso are good options for travelers with little time that would like to purchase some to-go items.

  • Does Logan International Airport have a prayer room?

    Logan International Airport has the Our Lady of the Airways Chapel that is located in Terminal C of the Arrivals level. It is open during standard business hours and is available to all travelers, no matter what their spiritual affiliation is.

  • What is the cheapest flight from Chicago to Boston?

    In the last 3 days, the lowest price for a flight from Chicago to Boston was $31 for a one-way ticket and $92 for a round-trip.

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

    A passport is not required to fly from Chicago to Boston.

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

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

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

    All the following airlines offer inflight Wi-Fi service on the Chicago to Boston flight route: American Airlines, Delta, JetBlue, Iberia, British Airways, and Finnair.

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

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

  • Which airline alliances offer flights from Chicago to Boston?

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

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

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

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

    The two airlines most popular with KAYAK users for flights from Chicago to Boston are Southwest and Delta. With an average price for the route of $224 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 $247 and an overall rating of 8.0.

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

    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 Chicago to Boston.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Boston from Chicago 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 Chicago to Boston?

    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 Boston with an airline and back to Chicago with another airline.

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

    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 Boston from Chicago 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 Chicago to Boston

  • Looking for a cheap flight? 25% of our users found flights on this route for $84 or less one-way and $191 or less round-trip.
  • Travelers flying American Airlines from Chicago to Boston should remember that the airline’s hub is at Boston Logan International Airport (BOS). You’ll arrive through Terminal B, and the airline’s Admirals Club is located at the same terminal. Members and holders and registered cards enjoy unrestricted access to this amenity. However, Economy Class travelers can access it at a reduced cost.
  • If you’re departing to BOS via Chicago Midway International Airport (MDW), you’ll find a road system between the terminal and the secure area. Inter-terminal movement between the two buildings is through a pedestrian bridge. However, every traveler must be cleared at the security checkpoint in the terminal building on the way out to the concourse.
  • Suppose you’re flying aboard Delta Airlines from Chicago O’Hare International Airport (ORD) to Boston Logan International Airport (BOS). In that case, you’ll be glad to note that the carrier allows pets such as cats and dogs in the cabin. Nevertheless, your four-legged friends must bear certified vaccination certificates and relevant health licenses. Still, it would help if you confined them in their cages to prevent them from disturbing other passengers.
  • Chicago Midway International Airport (MDW) sits about 10.7 miles from Downtown Chicago, and several public transportation options travel between the two destinations. The most convenient commute from downtown Chicago to MDW is via the Orange Line train. The train regularly plies between the two points, covering the distance in approximately 20-25min.
  • Before your trip from Chicago to BOS, you might wish to have a private session with the Almighty. Those departing through ORD will be glad to know that this prayer suite is tucked away from the noisy terminals. The airport’s chapel lies on the Mezzanine level of Terminal 2, atop the Delta Air Lines ticket desk.
  • If you’re looking at flights from Chicago to Boston, there are two different airports that you can fly out of. O'Hare International Airport is the largest airport in the region and harbors a high concentration of flights, while Chicago Midway International Airport is a smaller choice that is located only several miles from the city’s downtown.
  • Hoping to have a direct flight from Chicago to Boston? There are several major airlines that you can choose from. Southwest Airlines is popular amongst travelers with a large amount of luggage, as they allow you to check up to two bags for free, while Delta Airlines offers many upgrade options for those who would prefer more comfortable chairs or extra legroom.
  • For those that are traveling with kids, make sure to stop by one of the several children’s play areas located in Logan International Airport. These play areas are free for all travelers and feature a variety of toys, games, and activities that will help kids (and their parents) unwind after a long day of traveling.
  • To help pass the time before your flight takes off from O'Hare International Airport, see if you can access one of the airport’s private lounges. American, United, and Delta Airlines all have lounges in Chicago, and they often provide complimentary or reduced price access passes for their customers.
  • Flying can sometimes be stressful, so make sure you’re taking the time to unwind before boarding your plane. O'Hare International Airport has both a fitness club and a yoga room, both of which are perfect ways to let off some steam and relax before embarking on a day of traveling.
See more tips

Prefer to fly non-stop from Chicago to Boston?

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

Nonstop departures

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, +22 more

ANA, Air New Zealand, +23 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

Nonstop returns

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, +20 more

ANA, Air New Zealand, +21 more

Wednesday

ANA, Air New Zealand, Alaska Airlines, +19 more

ANA, Air New Zealand, +20 more

Thursday

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

ANA, Air New Zealand, +22 more

Friday

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

ANA, Air New Zealand, +24 more

Saturday

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

ANA, Air New Zealand, +21 more

Sunday

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

ANA, Air New Zealand, +23 more

See more direct flights
See more direct flights

Top 5 airlines serving from Chicago to Boston

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Boston. 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 Chicago to Boston? 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 8814 reviews
8.2Boarding
8.5Crew
7.9Entertainment
7.9Comfort
7.3Food
Airline reviews

Most of my discomfort was going through TSA. However, the Delta seats had inadequate leg room and I tried my very best to connect to the wi-fi and it was a cumbersome process that finally gave me the info that I needed to sign in AFTER I had completed the flight...Why make it so difficult to use? That said I really really appreciate the pilot taking a little extra time to avoid a bad storm area and both landings in Atlanta and Orlando were flawless to my delight!!!

6.0 GoodSus, Nov 2024GEG - ATL
Read more Delta reviews

Most of my discomfort was going through TSA. However, the Delta seats had inadequate leg room and I tried my very best to connect to the wi-fi and it was a cumbersome process that finally gave me the info that I needed to sign in AFTER I had completed the flight...Why make it so difficult to use? That said I really really appreciate the pilot taking a little extra time to avoid a bad storm area and both landings in Atlanta and Orlando were flawless to my delight!!!

Delayed in taking off because no flight crew. The in seat entertainment was working properly.

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 food was good. I ate gnocchi with marinara sauce and cheese, salted caramel tiramisu. And later in the trip cheese calzone. I watched 3 movies. The selection is really good. Have new and old movies. The flight attendances were nice and cordially. Overall the 6 hours trip was really pleasant ☺️. Planning the next trip.

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

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.

I paid for the service of having the right to choose my seat and it was not like that, they put me where they wanted and I explained to one of the staff that they were before boarding and they were very rude. I am traveling with the family and they put us in separate seats.

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.

Great! I love Jet Blue. My favorite airline! Very efficient, clean and timely.

We were told that our flight would be delayed for 90+ minutes because of weather, so we went to get something to eat only to have them randomly start boarding 15 minutes after the announcement, with no warning.

Entertainment... No earphones passed out. Many including me couldn't use the TV. Legroom was good. Crew was indifferent and a bit surly. Free wifi was a nice convenience. Check in desk location was unknown. Gate number on the boarding passes was wrong.

Confusing. Delay updates were out of whack At one point it said my flight was 25 hours. Three gate changes and two delays only to change back to original departure time. Gate announcer and on board flight attendant (Alejandro) making the announcements was impossible to understand due to accent and speed of speech. After beverage service the rear flight attendants sat back there on their phones. No refills no checking in, one sweep through for trash collection. Very impersonal. Bring back Coke products

Business class is great. New airplane, very comfortable, better than some of the major airlines I am used to

Delayed by almost an hour - I also noticed that all JetBlue flights departing from PBI were delayed yet the weather was perfect.

They need to improve their boarding process. Group 1 and/or paying first class passengers shouldn't be in the middle of boarding process

late departure due to some unspecified issue with ventilating the cabin. They got it running but it was FREEZING for the whole flight. I asked for a blanket but they didn't provide one. They could not turn up the heat. it was quite miserable.

Excellent staff helping my 96 year old senior promptly with her oxygen needs

Good even though flight was delayed, the crew was prompt and efficient.

I still prefer Delta, but Delta doesn’t fly to State College PA.

Everything was fantastic. Modern plane. All the amenities! Although the paid snacks and meals are pure robbery. Like i understand airlines need to make money, but 11$ USD for an overnight oats with some nuts in it and barely any pieces of apple.... Highway robbery

The flight was bumpy. No Breakfast or coffee was served, not even a bottle of water. The food was okay but odd. Rice with peas instead of couscous with some unknown green thing. United Airlines did not tell me that there was VERY LIMITED HANDICAP SERVICE IN NAPLES. De-plane via 20 aluminum steps. Taken to Van. You must walk into the terminal, find luggage, and then walk out to the rental car pickup spot that is 1 block from the terminal.

Crew did their best but the plane configuration is too tight if you're bigger than an average sardine. Controls for the entertainment system didn't all work. The aircraft hadn't been cleaned in awhile.

Didn't make it dir to delays - no support from United staff

This flight was 2.5 hours delayed due to crew issues. This meant that we arrived after 2 AM. Very very inconvenient and we were not really kept well informed.

The experience was good! I did not try any food, or in house entertainment. I don’t believe there were any tvs. Nothing major that stood out, but low key and good! Thanks!!

No food, no entertainment. But the flight was really short so maybe they had to skip drinks. I was able to board early ONLY because I am old and decrepit and they let me pre-board. I RESENT your dumping us into category 9 if we do not pay up. And when I paid for a seat I was STILL given 9. The pre-boarding helps. THIS flight was exceptionally smooth, please congratulate the pilots.

I had a TERRIBLE experience with the AA crew. I believe it was disability-related. It’s unlikely I will fly AA again.

Baby cried a lot. Nothing anyone could do about it. Just part of flying.

The flight crew was fantastic! Which the seats had a small TV.

The flight was delayed till next day ! They kept delaying every 30 minutes then after 3 hours they delayed it till next day. We kept waiting in line standing more than an hour to get the hotel and meal vouchers. There was no communication at all. Everything was bad

Smoothe flight. Pilot and crew did a great job. Uncomfortable seat in this jet, felt worn out

Free WiFi and movies were not free - everything required signing up for future billing. Boston bound crew were very courteous and gracious.

seats were way too small. Too short of a flight to offer amenities.

The main problem was delay. The plane was at the gate early and bags were loaded. However, there was no crew for the flight. They were inbound from LGA and had to land and make their way to our gate. It took more than 40 minutes. Then, once the crew arrived and boarded, one of the crew members had to deplane and then a replacement crew member had to be found. It took another 40 minutes or so to get the final crew member. In all, we took off about 2 hours later than our scheduled departure time. Once in the air, the flight was great. Smooth most of the way. The crew was professional and efficient.

Easy! As long as you don’t mind no frills, our flight was enjoyable and on time

Fantastic. Had handicapped traveler and they helped us through security, helped with boarding, helped put wheelchair together, and were all very patient. A pleasant change from previous spirit flights I’ve taken. Highly recommend.

No frills, cheap price & flight was on time, I'm happy.

Flight delayed. Seat assignment doesn’t get assign until last minute. Seats don’t recline and very stiff

The flight was delayed, and we waited for more than an hour on the plane.

Could at least have little recline in economy seats and windows to the last row, they were super uncomfortable and lots of chit chat and disturbance from the operation of crew members and other passengers

Was told by one of the helpers at spirit in Detroit that I had to pay for my bag that could fit on the over head bin after I asked her repeatedly well what about the over head bin can’t my bag fit in there she said no I had to check it. Then sent me the long way to the tsa when my gate was the other way. I didn’t have that problem in Chicago.

Cancelled after 3 hour delay with no aside from a rebooking three days later.

Nothing. Will never ever travel on Spirit or Frontier. Both of them Garbage Airlines.

There was no water offered to passengers during a four hour flight, five hours on the plane. There is no entertainment on board. The crew interrupt everyone often to sell credit cards and reward packages. Other than that, pretty typical flight. You get what you pay for.

Book cheap flights from Chicago to Boston

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to Boston found on KAYAK in the last 72 hours.
11/24Sun
nonstopSpirit Airlines
2h 19mORD-BOS
$31
11/24Sun
nonstopSpirit Airlines
2h 19mORD-BOS
$37
1/9Thu
nonstopDelta
2h 35mORD-BOS
$79
12/10Tue
1 stopJetBlue
7h 31mORD-BOS
$88
1/12Sun
nonstopJetBlue
2h 15mORD-BOS
$89
12/24Tue
nonstopDelta
2h 28mORD-BOS
$90
1/7Tue
nonstopUnited Airlines
2h 23mORD-BOS
$114
12/21Sat
nonstopUnited Airlines
2h 24mORD-BOS
$115
11/17Sun
nonstopAmerican Airlines
2h 19mORD-BOS
$126
11/16Sat
1 stopAmerican Airlines
6h 02mORD-BOS
$133

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Last minute flights from Chicago to Boston

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 Chicago to Boston that are departing in the next 10 days.
11/14Thu
multi-stop
4h 26mORD-BOS
11/19Tue
nonstop
3h 10mBOS-ORD
$109
11/14Thu
multi-stop
4h 26mORD-BOS
11/19Tue
nonstop
3h 10mBOS-ORD
$110
11/13Wed
multi-stopFrontier
9h 02mORD-BOS
11/23Sat
multi-stopFrontier
13h 53mBOS-ORD
$114
11/14Thu
nonstopSpirit Airlines
2h 18mORD-BOS
11/19Tue
nonstopSpirit Airlines
3h 10mBOS-ORD
$160
11/15Fri
multi-stopSpirit Airlines
24h 02mORD-BOS
11/19Tue
multi-stopSpirit Airlines
7h 30mBOS-ORD
$170
11/15Fri
nonstopUnited Airlines
2h 25mORD-BOS
11/16Sat
nonstopUnited Airlines
2h 56mBOS-ORD
$247
11/14Thu
nonstopDelta
2h 30mORD-BOS
12/6Fri
nonstopDelta
3h 03mBOS-ORD
$252
11/14Thu
multi-stopDelta
4h 20mORD-BOS
12/6Fri
nonstopDelta
2h 58mBOS-ORD
$262
11/13Wed
nonstopJetBlue
2h 22mORD-BOS
11/17Sun
nonstopJetBlue
3h 06mBOS-ORD
$297
11/13Wed
nonstopJetBlue
2h 22mORD-BOS
11/18Mon
multi-stopJetBlue
5h 02mBOS-ORD
$306

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

Information on your arrival and departure airports

Compare transportation modes for Chicago to Boston

Average priceAverage duration
Flights$3532h 10m
Trains$28822h 01m