Cheap flights from Boston to Chicago from $49

Round-trip
1 adult
Economy
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Tue 2/1
Tue 2/8

Deals available from 900+ travel sites.

Travel Restriction Alert

The COVID-19 (coronavirus) outbreak may impact travel from Boston Logan Intl to Chicago.
View current United States travel restrictions

Flight information for Boston to Chicago
(BOS to CHI)

Find info about flight duration, direct flights, and airports for your flight from Boston to Chicago
Best Price Found$49The best one-way flight to Chicago from Boston in the past 72 hours is $49. The best round-trip flight deal from Boston to Chicago found on momondo in the last 72 hours is $98.
Fastest flight time2h 57mThe fastest flight from Boston to Chicago takes 2h 57m
Direct flightsMon, Tue, Wed, Fri, Sat and SunDirect flights go from Boston to Chicago on Monday, Tuesday, Wednesday, Friday, Saturday and Sunday. The only airline offering direct flights is American Airlines.
Airports in Chicago3 airportsThere are 3 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW), Chicago Greater Rockford (RFD)

How to get the cheapest flight ticket from Boston to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

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

August

The cheapest time of year to fly to Chicago from Boston is August. Most expensive is December

What is the cheapest day to depart Boston for Chicago?

Saturday

The cheapest day of the week is typically Saturday. The most expensive is typically Sunday

When is the cheapest time to fly from Boston to Chicago?

at noon

Boston to Chicago flights are approximately 36% more expensive in the afternoon than at noon

What is the cheapest airline that flies to Chicago from Boston?

Spirit Airlines

American Airlines, Delta, and JetBlue are the most popular carriers operating from Boston to Chicago

What is the cheapest Boston to Chicago flight route?

Boston Logan Intl - Chicago O'Hare Intl

Fly from Boston Logan Intl to Chicago O'Hare Intl for the best Boston - Chicago flight prices

How far in advance should you book Boston to Chicago flights?

0 days before

The cheapest time to buy a flight from Boston to Chicago is approximately 0 days to departure


Easily compare round-trip flights from Boston to Chicago

Below you can see the best fares for your round-trip flight route over the next three months. All fares were found on momondo this week. Browse the quickest and cheapest flights from Boston to Chicago by changing tabs
American Airlines
Feb 11
BOS11:45 amBoston Logan Intl
2h 54m
ORD2:39 pmChicago O'Hare Intl
Feb 11
ORD3:06 pmChicago O'Hare Intl
2h 11m
BOS5:17 pmBoston Logan Intl
Multiple Airlines
Feb 7
BOS11:45 amBoston Logan Intl
2h 54m
ORD2:39 pmChicago O'Hare Intl
Feb 14
ORD3:10 amChicago O'Hare Intl
2h 11m
BOS5:21 amBoston Logan Intl
JetBlue
Feb 16
BOS12:56 amBoston Logan Intl
3h 01m
ORD3:57 amChicago O'Hare Intl
Feb 17
ORD3:10 amChicago O'Hare Intl
2h 11m
BOS5:21 amBoston Logan Intl
Spirit Airlines
Feb 8
BOS3:26 amBoston Logan Intl
30h 01m
1 stop
ORD9:27 amChicago O'Hare Intl
Feb 15
ORD1:30 amChicago O'Hare Intl
12h 29m
1 stop
BOS1:59 pmBoston Logan Intl
Delta
Feb 17
BOS4:00 amBoston Logan Intl
6h 43m
1 stop
ORD10:43 amChicago O'Hare Intl
Feb 20
ORD1:15 amChicago O'Hare Intl
2h 30m
BOS3:45 amBoston Logan Intl
United Airlines
Mar 3
BOS4:45 amBoston Logan Intl
2h 57m
ORD7:42 amChicago O'Hare Intl
Mar 6
ORD2:16 amChicago O'Hare Intl
7h 14m
1 stop
BOS9:30 amBoston Logan Intl

Find the cheapest one-way flights from Boston to Chicago

If you're looking for one-way flights from Boston to Chicago, view some of our deals below provided by Delta, JetBlue and Spirit Airlines
JetBlue
Feb 5
BOS4:52 amBoston Logan Intl
3h 08m
ORD8:00 amChicago O'Hare Intl
Spirit Airlines
Feb 16
BOS12:45 amBoston Logan Intl
13h 52m
1 stop
ORD2:37 pmChicago O'Hare Intl
Multiple Airlines
Mar 2
BOS3:55 amBoston Logan Intl
14h 35m
1 stop
ORD6:30 pmChicago O'Hare Intl

Search last-minute flights to Chicago from Boston

Find and compare round-trip flight prices for your last-minute flight from Boston to Chicago
JetBlue
Feb 5
BOS4:52 amBoston Logan Intl
3h 08m
ORD8:00 amChicago O'Hare Intl
Feb 5
ORD10:08 amChicago O'Hare Intl
2h 25m
BOS12:33 pmBoston Logan Intl
Spirit Airlines
Feb 1
BOS3:26 amBoston Logan Intl
30h 01m
1 stop
ORD9:27 amChicago O'Hare Intl
Feb 8
ORD1:30 amChicago O'Hare Intl
12h 29m
1 stop
BOS1:59 pmBoston Logan Intl
Multiple Airlines
Feb 2
BOS1:40 amBoston Logan Intl
3h 17m
ORD4:57 amChicago O'Hare Intl
Mar 6
ORD1:46 amChicago O'Hare Intl
2h 22m
BOS4:08 amBoston Logan Intl
Delta
Feb 1
BOS3:30 amBoston Logan Intl
6h 25m
1 stop
ORD9:55 amChicago O'Hare Intl
Feb 1
ORD12:55 pmChicago O'Hare Intl
5h 59m
1 stop
BOS6:54 pmBoston Logan Intl
Frontier
Feb 4
BOS1:05 pmBoston Logan Intl
2h 55m
MDW4:00 pmChicago Midway
Feb 6
MDW3:55 amChicago Midway
4h 35m
1 stop
BOS8:30 amBoston Logan Intl
JetBlue
Feb 4
BOS12:00 amBoston Logan Intl
2h 59m
ORD2:59 amChicago O'Hare Intl
Feb 6
ORD3:10 amChicago O'Hare Intl
2h 11m
BOS5:21 amBoston Logan Intl

Best airlines flying from Boston to Chicago

Compare and see reviews for airlines that fly from Boston to Chicago with momondo
AirlineRatingFree CancellationPrice
Spirit Airlines
PriceFrom $56
Free Cancellation
Rating
6.3
6.4

Boarding

6.0

Comfort

6.9

Crew

5.0

Entertainment

5.3

Food

Reviews

To whom may concern, I was not able to board my flight because it showed as cancel but my credit card got charge. Please issue refund. Thank You Jan Pierre Rivera

1 / 10
Delta
PriceFrom $68
Free Cancellation
Rating
8.0
8.1

Boarding

8.1

Comfort

8.2

Crew

7.9

Entertainment

7.7

Food

Reviews

Even after posting extra for comfort +, the seats do not recline!

1 / 10
JetBlue
PriceFrom $71
Free Cancellation
Rating
7.2
7.4

Boarding

7.7

Comfort

8.0

Crew

7.3

Entertainment

6.9

Food

Reviews

Smooth trip. No problems no delays and that's great.

1 / 10
American Airlines
PriceFrom $77
Free Cancellation
Rating
7.2
7.4

Boarding

7.1

Comfort

7.8

Crew

7.1

Entertainment

6.8

Food

Reviews

Flight attendant for first class is definitely not a morning person. Oh and the WiFi DID NOT WORK!

1 / 10
United Airlines
PriceFrom $80
Free Cancellation
Rating
7.3
7.5

Boarding

7.1

Comfort

7.8

Crew

7.0

Entertainment

6.7

Food

Reviews

2 hour delay and then 15 min taxi to the gate just to be told a big pile of snow was blocking the gate.

1 / 10
Southwest
PriceFrom $185
Free Cancellation
Rating
7.9
8.0

Boarding

7.9

Comfort

8.3

Crew

7.5

Entertainment

7.0

Food

Reviews

Pros: Fast boarding

Cons: On arrival, have passengers needing assistance to wait to deplane until the end.

1 / 10

JetBlue flights from Boston to Chicago

Our best JetBlue deals on Boston to Chicago flight tickets
JetBlue
Feb 5
BOS4:52 amBoston Logan Intl
3h 08m
ORD8:00 amChicago O'Hare Intl
Feb 5
ORD10:08 amChicago O'Hare Intl
2h 25m
BOS12:33 pmBoston Logan Intl
JetBlue
Feb 16
BOS12:56 amBoston Logan Intl
3h 01m
ORD3:57 amChicago O'Hare Intl
Feb 17
ORD3:10 amChicago O'Hare Intl
2h 11m
BOS5:21 amBoston Logan Intl
JetBlue
Feb 9
BOS12:42 amBoston Logan Intl
5h 32m
1 stop
ORD6:14 amChicago O'Hare Intl
Feb 9
ORD7:49 amChicago O'Hare Intl
2h 24m
BOS10:13 amBoston Logan Intl

Delta flights from Boston to Chicago

Our best Delta deals on Boston to Chicago flight tickets
Delta
Feb 17
BOS4:00 amBoston Logan Intl
6h 43m
1 stop
ORD10:43 amChicago O'Hare Intl
Feb 20
ORD1:15 amChicago O'Hare Intl
2h 30m
BOS3:45 amBoston Logan Intl
Delta
Feb 25
BOS1:40 amBoston Logan Intl
3h 17m
ORD4:57 amChicago O'Hare Intl
Feb 28
ORD3:26 pmChicago O'Hare Intl
2h 26m
BOS5:52 pmBoston Logan Intl
Delta
Feb 8
BOS12:45 amBoston Logan Intl
6h 58m
1 stop
ORD7:43 amChicago O'Hare Intl
Feb 8
ORD10:43 amChicago O'Hare Intl
5h 33m
1 stop
BOS4:16 pmBoston Logan Intl

  • Are airlines flying from Boston Logan Intl to Chicago offering flexible cancellation due to COVID-19?

    Due to the global impact of COVID-19, some of our airline partners operating flights from Boston Logan Intl to Chicago, such as United Airlines, American Airlines, and JetBlue may have put in place flexible cancellation policies. Use our site to search for all of the airlines offering this flexibility to you.

  • How far is Boston Logan Intl to Chicago by plane?

    A flight from Boston Logan Intl to Chicago will travel around 847.9 mi. 2h 45m is a normal flight duration for this route.


Can I fly to Chicago from Boston Logan Intl right now?

Information is based on travel restrictions for travel to Chicago within the United States

Most visitors from Boston Logan Intl need to provide a negative COVID-19 test result and/or quarantine to enter Chicago.

COVID-19 testing requirements
Visitors from Boston Logan Intl must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 24 hours before departing to Chicago.

Quarantine requirements
Visitors from Boston Logan Intl are not required to quarantine after entering Chicago.

Can I fly back to Boston Logan Intl from Chicago?

Returning to Boston Logan Intl from Chicago

COVID-19 testing requirements
Visitors from Chicago must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 24 hours before departing to Boston Logan Intl.

Quarantine requirements
Visitors from Chicago are not required to quarantine after entering Boston Logan Intl.

If you are planning to travel to Chicago at this time, it is recommended that you stay up to date on current restrictions and follow proper safety measures while in public.

Alternative routes for Boston to Chicago

Compare alternative flights to and from nearby airports and cities to discover the best prices and most convenient flight times
Boston to St. Louis Flights
Fastest flight time3h 05m
Cheapest price$114

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