Cheap flights from Boston to Chicago

Round-trip
Economy
Boston (BOS)
Chicago (CHI)
Sun 2/21
Sun 2/28
Any month
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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 $69 The best flight deal from Boston to Chicago found on momondo in the last 72 hours is $69
Fastest flight time 3h 10m The fastest flight from Boston to Chicago takes 3h 10m.
Direct flights Tu Direct flights go from Boston to Chicago on Tuesday. Airline offering direct flights is United Airlines..
Airports in Chicago 3 airports There 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 30% more expensive in the afternoon than at noon
What is the cheapest airline that flies to Chicago from Boston?
Spirit Airlines
Spirit Airlines, Envoy Air, and Delta 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?
3 days before
The cheapest time to buy a flight from Boston to Chicago is approximately 3 days to departure
60
Days before departure
0

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
Spirit Airlines
Apr 30
2h 50m
Boston Logan Intl
2h 50m
11:37 am
Chicago O'Hare Intl
May 3
11:22 am
Chicago O'Hare Intl
2h 23m
1:45 pm
Boston Logan Intl
Spirit Airlines
May 13
2h 50m
Boston Logan Intl
2h 50m
11:37 am
Chicago O'Hare Intl
May 18
11:22 am
Chicago O'Hare Intl
2h 23m
1:45 pm
Boston Logan Intl
Multiple Airlines
Mar 10
7h 51m
Boston Logan Intl
7h 51m
1 stop
8:51 am
Chicago O'Hare Intl
Mar 30
2:00 am
Chicago O'Hare Intl
2h 27m
4:27 am
Boston 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 Spirit Airlines
Spirit Airlines
Apr 20
2h 50m
Boston Logan Intl
2h 50m
11:37 am
Chicago O'Hare Intl
Spirit Airlines
Apr 16
2h 50m
Boston Logan Intl
2h 50m
11:37 am
Chicago O'Hare Intl
American Airlines
Feb 9
3h 05m
Boston Logan Intl
3h 05m
11:55 am
Chicago O'Hare 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
5.6
6.1

Boarding

5.4

Comfort

6.5

Crew

4.6

Entertainment

4.7

Food

Reviews

Pros: Price, but know what to expect.

Cons: Spirit charges even for water.

1 / 10
Delta
PriceFrom $68
Free Cancellation
Rating
7.9
8.1

Boarding

7.8

Comfort

8.5

Crew

7.8

Entertainment

7.5

Food

Reviews

Cons: The flight attendants were fantastic!

1 / 10
JetBlue
PriceFrom $71
Free Cancellation
Rating
8.1
8.3

Boarding

8.2

Comfort

8.6

Crew

7.9

Entertainment

7.8

Food

Reviews

Pros: Most of the basics were good.

Cons: The flight was substantially delayed and when we got to Chicago we had to wait a long time for a gate agent so that we could deplane because only one gate agent was working at that hour (10:20 p.m.). Also, the flight delay notifications came after I was close to the airport and at the airport--earlier notifications (if possible) would help. The tv/movie portion of the entertainment was not working at all.

1 / 10
American Airlines
PriceFrom $77
Free Cancellation
Rating
7.2
7.5

Boarding

7.1

Comfort

7.8

Crew

6.8

Entertainment

6.7

Food

Reviews

Pros: I didn’t like anything at all

Cons: They have to add electronic devices or charge plug on it

1 / 10
United Airlines
PriceFrom $80
Free Cancellation
Rating
7.0
7.4

Boarding

6.9

Comfort

7.7

Crew

6.5

Entertainment

6.4

Food

Reviews

Pros: Direct flight

Cons: Forced to check in carry on, 1 hour to get it at bagage claim.

1 / 10
Southwest
PriceFrom $185
Free Cancellation
Rating
8.4
8.7

Boarding

8.4

Comfort

9.0

Crew

8.0

Entertainment

7.8

Food

Reviews

Pros: Price

Cons: No tv to track the flight progress

1 / 10

Which airlines flying from Boston Logan Intl to Chicago have COVID-19 safety policies in place?

Airlines such as Delta have taken additional precautions to make sure you’re safer while traveling. When flying from Boston Logan Intl to Chicago, expect masks to be provided - they are required onboard. Aircrafts are also being cleaned thoroughly with enhanced products regularly. Additional policies include the installation of HEPA filters and pre-flight testing. Some airlines are even offering socially-distanced seating for a limited time. Keep in mind that policies will vary by airline.

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.


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