Boston to Chicago Flights

Boston to Chicago Flight Info

Peak season for travel

November
US$47

Off-season for travel

June
US$101

Cheapest return ticket price

US$119
Boston(BOS) ⇒ Chicago(MDW)

Cheapest direct flight price

US$73
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$110.
  • 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 05:48 and arrives in Chicago (ORD) at 07:55.
  • What time does the latest flight from Boston to Chicago depart?

    The latest flight departs from Boston (BOS) at 20:46 and arrives in Chicago (ORD) at 22:38.
  • 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 294 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

05:00

BOS

07:05

ORD

Boston to Chicago---W-F-Search

06:00

BOS

07:41

ORD

Boston to ChicagoS------Search

06:28

BOS

08:23

ORD

Boston to Chicago------SSearch

06:54

BOS

08:54

ORD

Boston to Chicago---W---Search

07:00

BOS

09:00

ORD

Boston to Chicago-M---FSSearch

07:41

BOS

09:44

ORD

Boston to ChicagoS------Search

09:00

BOS

11:00

ORD

Boston to ChicagoS--WT-SSearch

09:01

BOS

10:59

ORD

Boston to ChicagoSMTWTF-Search

10:00

BOS

12:00

ORD

Boston to Chicago-M-----Search

10:30

BOS

12:27

ORD

Boston to Chicago------SSearch

10:35

BOS

12:16

ORD

Boston to ChicagoS------Search

12:00

BOS

13:41

ORD

Boston to Chicago------SSearch

12:01

BOS

14:01

ORD

Boston to Chicago-------Search

12:51

BOS

14:49

ORD

Boston to ChicagoSMTWTFSSearch

13:25

BOS

15:20

ORD

Boston to ChicagoSMTWTFSSearch

13:30

BOS

15:28

ORD

Boston to ChicagoSMTWTFSSearch

13:35

BOS

15:16

ORD

Boston to Chicago----T--Search

13:45

BOS

15:44

ORD

Boston to Chicago-------Search

15:00

BOS

17:03

ORD

Boston to Chicago-------Search

17:00

BOS

19:18

ORD

Boston to ChicagoSMTWTFSSearch

17:04

BOS

19:20

ORD

Boston to ChicagoSMTWTFSSearch

17:15

BOS

19:18

ORD

Boston to Chicago-------Search

17:28

BOS

19:35

ORD

Boston to ChicagoSMTWTFSSearch

18:15

BOS

20:13

ORD

Boston to Chicago------SSearch

AD7019

Azul

18:22

BOS

20:22

ORD

Boston to Chicago------SSearch

18:35

BOS

20:16

ORD

Boston to Chicago-------Search

19:10

BOS

21:09

ORD

Boston to ChicagoSMTWTFSSearch

19:14

BOS

21:25

ORD

Boston to ChicagoS------Search

19:15

BOS

21:23

ORD

Boston to Chicago-------Search

19:22

BOS

21:30

ORD

Boston to Chicago-------Search
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