Boston to Chicago Flights

Boston to Chicago Flight Info

Peak season for travel

June
US$127

Off-season for travel

September
US$46

Cheapest return ticket price

US$304
Boston(BOS) ⇒ Chicago(MDW)

Cheapest direct flight price

US$156
Boston(BOS) ⇒ Chicago(ORD)

Frequently Asked Questions

  • When are flight tickets from Boston (BOS) to Chicago (CHI) the cheapest?

    Airlines adjust prices for flights from Boston to Chicago based on the date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.
  • How much do flights from Boston (BOS) to Chicago (CHI) cost?

    According to Trip.com's data, the lowest price is around US$246.
  • How long does it take to fly from Boston (BOS) to Chicago (CHI)?

    It takes about 2 hours 56 minutes to fly from Boston (BOS) to Chicago (CHI).
  • What is the transportation method from the main airport to downtown in Chicago?

    • The distance from O'Hare International Airport to downtown is about 25km, by taxi about 40 minutes.
    • The distance from Midway International Airport to downtown is about 13km, by taxi about 30 minutes.
  • What time does the earliest flight from Boston to Chicago depart?

    The earliest flight departs from Boston (BOS) at 05:15 and arrives in Chicago (ORD) at 07:13.
  • What time does the latest flight from Boston to Chicago depart?

    The latest flight departs from Boston (BOS) at 20:12 and arrives in Chicago (ORD) at 22:02.
  • What are the most popular airlines that fly from Boston (BOS) to Chicago (CHI)?

    Airlines with flights from Boston (BOS) to Chicago (CHI): United Airlines, Jetblue Airways, American Airlines, Japan Airlines and Spirit Airlines.
  • What's the most popular airline for non-stop flights from Boston (BOS) to Chicago (CHI)?

    United Airlines operates 381 non-stop flights from Boston (BOS) to Chicago (CHI).
  • How many airports are there in Chicago (CHI)?

  • What are some travel guidelines for Chicago during the COVID19 pandemic?

    Entry restrictions and flight schedule changes and cancellations are frequently updated and subject to change. If you plan to travel to Chicago, please obtain the most updated information from the airline you plan to book your travels with. You can also refer to COVID19 Country/Region Entry Restrictions for more information.
  • Which airlines offer free date changes for flights to this city during the COVID19 pandemic?

    There are no airlines with flights to this city that provide this service. Please use this information as a reference only and confirm with the airline prior to booking.

Boston (BOS) to Chicago (CHI) Flight Schedule

Flight info.
Departure
Arrival
RouteWeekly Schedule
American Airlines

05:00

BOS

07:05

ORD

Boston to Chicago---W-F-Search
American Airlines

06:00

BOS

07:41

ORD

Boston to ChicagoSMTW-FSSearch
Jetblue Airways

06:28

BOS

08:23

ORD

Boston to Chicago------SSearch
Alaska Airlines

06:54

BOS

08:54

ORD

Boston to Chicago---W---Search
United Airlines

07:00

BOS

09:00

ORD

Boston to Chicago----TF-Search
American Airlines

07:41

BOS

09:44

ORD

Boston to ChicagoS------Search
Japan Airlines

09:00

BOS

11:00

ORD

Boston to ChicagoSMTW-FSSearch
American Airlines

09:01

BOS

10:59

ORD

Boston to ChicagoSMTWTF-Search
United Airlines

10:00

BOS

12:00

ORD

Boston to Chicago----T--Search
American Airlines

10:30

BOS

12:27

ORD

Boston to Chicago------SSearch
American Airlines

10:35

BOS

12:16

ORD

Boston to ChicagoS------Search
American Airlines

12:00

BOS

13:41

ORD

Boston to Chicago------SSearch
American Airlines

12:01

BOS

14:01

ORD

Boston to Chicago-------Search
United Airlines

12:51

BOS

14:49

ORD

Boston to Chicago-----F-Search
Spirit Airlines

13:25

BOS

15:20

ORD

Boston to ChicagoSMTWTFSSearch
American Airlines

13:30

BOS

15:28

ORD

Boston to ChicagoSMTWTFSSearch
American Airlines

13:35

BOS

15:16

ORD

Boston to Chicago----T--Search
American Airlines

13:45

BOS

15:44

ORD

Boston to Chicago-------Search
American Airlines

15:00

BOS

17:03

ORD

Boston to Chicago-------Search
American Airlines

17:00

BOS

19:18

ORD

Boston to ChicagoSMTWTFSSearch
American Airlines

17:04

BOS

19:20

ORD

Boston to ChicagoSMTWTFSSearch
American Airlines

17:15

BOS

19:18

ORD

Boston to Chicago-------Search
American Airlines

17:28

BOS

19:35

ORD

Boston to ChicagoSMTWTFSSearch
United Airlines

18:15

BOS

20:13

ORD

Boston to Chicago------SSearch
Azul

18:22

BOS

20:22

ORD

Boston to Chicago------SSearch
American Airlines

18:35

BOS

20:16

ORD

Boston to Chicago-------Search
American Airlines

19:10

BOS

21:09

ORD

Boston to ChicagoSMTWTFSSearch
American Airlines

19:14

BOS

21:25

ORD

Boston to ChicagoS------Search
American Airlines

19:15

BOS

21:23

ORD

Boston to Chicago-------Search
American Airlines

19:22

BOS

21:30

ORD

Boston to Chicago-------Search
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  • Plan Your Trip from Boston (BOS) to Chicago (CHI)

    Chicago attracts thousands of visitors every year for both business and pleasure. Whether you’re taking a last-minute break or a much needed getaway, flights from Boston to Chicago on Trip.com can help you get there with ease. With Trip.com, you can browse popular airlines with flights to Chicago, check the best season to visit, and preview Chicago attractions before you arrive. With flight deals and exciting attractions waiting for you to explore in Chicago, the best time to book flights from Boston to Chicago is now! Planning a trip from Boston to Chicago is easy when you use Trip.com to help you make travel arrangements. Whether you are flying one-way, non-stop, or round-trip, you will find just the flight you need with us. If you want to lock in a great deal for your flights, go for a round-trip flight, if you need flexibility with your itinerary, book a one-way flight to Chicago. With Trip.com, you can search for available flights and hotel rooms, and then make your booking quickly and easily online and on the go. Pack your travel accessories, make a must-see bucket list, and book your flight to Chicago on Trip.com today!

  • A Trip to Remember (BOS—CHI)

    Make your journey from Boston (BOS) to Chicago (CHI) a trip to remember by using Trip.com to view Chicago attractions before you arrive. Once you know what to do in Chicago, you can reserve and book in advance for the best travel experience possible. Planning ahead is the most effective way to ensure your whole travel experience goes smoothly. Whether you need help choosing the perfect restaurant, discovering the best places to try local flavors, or finding the most stunning views in town, Trip.com is with you every step of the way for your trip to Chicago.