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Cheap Flights from Boston to Chicago

  • Boston Chicago

    Sat, 25 Apr - Fri, 1 May

    From £48.43
  • Boston Chicago

    Sat, 25 Apr - Fri, 1 May

    From £54.03
  • Boston Chicago

    Thu, 7 May - Wed, 13 May

    From £54.49
  • Boston Chicago

    Fri, 5 Jun - Mon, 8 Jun

    From £55.17
  • Boston Chicago

    Sat, 25 Apr - Fri, 1 May

    From £55.63
  • Boston Chicago

    Wed, 15 Apr - Wed, 22 Apr

    From £87.27

Prices shown are for 1 adult ticket including taxes & fees.(As ticket fares can change frequently, these advertised prices are for reference only. The actual prices will be shown at time of booking.)

Boston to Chicago Flight Information

Below are some common questions asked about this flight route:

When can I book the cheapest flight from Boston to Chicago?

Airlines adjust prices for plane tickets based on the day and time that you book your flight. After analyzing data from all airlines, we have discovered that the best days to book flights from Boston to Chicago are Tuesdays, Wednesdays, and Saturdays.

What are the airlines flying from Boston to Chicago?

What is the most popular airline for non-stop flights from Boston to Chicago?

American Airlines provides 44 of the non-stop flights between Boston and Chicago.

How many airports are there in Chicago?

Average duration of direct flights: 2h53m
Airports at destination:
Flight route:
Price starting from:

Boston to Chicago Flight Schedule

Flight info. Departure
Arrival
Weekly Schedule
18:15 BOS 20:13 ORD
SMTWTFS Search
06:28 BOS 08:23 ORD
S------ Search
10:00 BOS 12:00 ORD
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09:00 BOS 11:00 ORD
SMTWTFS Search
06:00 BOS 07:41 ORD
SMTWT-S Search
13:25 BOS 15:20 ORD
SMTWTFS Search
12:51 BOS 14:49 ORD
SMTWTFS Search
07:00 BOS 09:00 ORD
SMTWTFS Search
12:00 BOS 13:41 ORD
SMTWTF- Search
07:41 BOS 09:44 ORD
SMTWTFS Search
09:00 BOS 10:41 ORD
SMTWTFS Search
18:46 BOS 20:55 ORD
SMTWTFS Search
NH7479
ANA
08:30 BOS 10:20 ORD
SM----- Search
05:00 BOS 06:50 ORD
SMTW-F- Search
12:26 BOS 14:22 ORD
S------ Search
NH7787
ANA
10:12 BOS 11:58 ORD
SM----- Search
13:37 BOS 15:34 ORD
SMTWTFS Search
15:00 BOS 16:50 ORD
SMT-TFS Search
NH7481
ANA
07:12 BOS 09:02 ORD
SMTWTFS Search
05:00 BOS 06:44 ORD
--T--F- Search

Flights to Midway International Airport (MDW) from Boston

11 Apr, 05:45 - 13 Apr, 22:35
DL | Delta Air Lines
4h 12m
BOS - MDW
1 stop
£140
Round-trip from
Search

Flights to O'Hare International Airport (ORD) from Boston

25 Apr, 17:52 - 1 May, 06:00
NK | Spirit Airlines
2h 58m
BOS - ORD
Nonstop
£48
Round-trip from
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25 Apr, 08:00 - 1 May, 06:00
DL | Delta Air Lines
3h 2m
BOS - ORD
Nonstop
£54
Round-trip from
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7 May, 18:13 - 13 May, 17:02
B6 | Jetblue Airways
2h 43m
BOS - ORD
Nonstop
£54
Round-trip from
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5 Jun, 20:46 - 8 Jun, 20:28
AA | American Airlines
2h 56m
BOS - ORD
Nonstop
£55
Round-trip from
Search
25 Apr, 10:10 - 1 May, 06:00
UA | United Airlines
2h 52m
BOS - ORD
Nonstop
£56
Round-trip from
Search

Prices shown are for 1 adult ticket including taxes & fees.(As ticket fares can change frequently, these advertised prices are for reference only. The actual prices will be shown at time of booking.)

Roundtrip vs One-Way Flights from Boston to Chicago

There is usually no major price difference between buying a roundtrip flight versus a one-way flight. Increased flexibility is the main benefit when it comes to buying a one-way flight from Boston to Chicago. However, booking a roundtrip flight is a simpler process. You can compare roundtrip and one-way flights by using our flight comparison tool.

Direct vs Connecting Flights from Boston to Chicago

The average price for connecting flights from Boston to Chicago is GBP 96.39. The average price for nonstop flights from Boston to Chicago is GBP 110.59.

Travel from Boston to Chicago

Chicago attracts thousands of visitors every year for both business and pleasure. Planning a trip from Boston to Chicago is easy when you use Trip.com to help you make travel arrangements. With Trip.com, you can search for available flights and hotel rooms, and then make your booking quickly and easily online.

A Trip to Remember

Make your journey from Boston to Chicago a trip to remember when you use Trip.com to review city attractions before you arrive. With a preview of what's available at your destination, you can make any necessary reservations in advance for the best travel experience possible.

Trip.com is part of Trip.com Group Limited, one of the world's leading providers of travel services.
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