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Cheap flights from Boston to Chicago
Round-trip
Economy
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 | $54 | The best flight deal from Boston to Chicago found on momondo in the last 72 hours is $54 |
| Fastest flight time | 2h 50m | The fastest flight from Boston to Chicago takes 2h 50m |
| Direct flights | Th, Fr, Sa and Su | Direct flights go from Boston to Chicago on Thursday, Friday, Saturday and Sunday. The only airline offering direct flights is American 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 36% 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![Spirit Airlines]()
Sep 18![Spirit Airlines]()
Sep 22
BOS5:53 pmBoston Logan Intl
2h 33m
ORD8:26 pmChicago O'Hare Intl
ORD5:00 amChicago O'Hare Intl
2h 18m
BOS7:18 amBoston Logan Intl
Spirit Airlines![Spirit Airlines]()
Sep 11![Spirit Airlines]()
Sep 14
BOS5:53 pmBoston Logan Intl
2h 33m
ORD8:26 pmChicago O'Hare Intl
ORD5:00 amChicago O'Hare Intl
2h 18m
BOS7:18 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 Spirit Airlines
Best airlines flying from Boston to Chicago
Compare and see reviews for airlines that fly from Boston to Chicago with momondo
AirlineFree CancellationPrice
PriceFrom $56
Free Cancellation
Reviews
Pros: Well, it was not very comfortable and we were delayed for an hour. And a crew member was sick.
Cons: Mostly everything.
1 / 10
PriceFrom $68
Free Cancellation
Reviews
Cons: Wouldn't let us on the flight when there was plenty of time to get there. Manager was arrogant and slow - didn't care. Poor policies at that airport.
1 / 10
PriceFrom $71
Free Cancellation
Reviews
Pros: Wayne at the DCA Airport was gracious and amazing.
Cons: The planes still aren’t clean. Pretty sure something was growing on the seat in front of me.
1 / 10
PriceFrom $77
Free Cancellation
Reviews
Pros: Delayed flight no reasons seems like American Airlines don’t know what to do in these situations
Cons: I believe this airlines should have figured the answer to this question by now.
1 / 10
PriceFrom $80
Free Cancellation
Reviews
Cons: Sarasota ticketing agent was not very nice at all 😟 Houston Gate agent was not nice either. We were treated like we were stupid for asking questions. I hope it’s not racism issues. I wished I had taken their names.
1 / 10
PriceFrom $185
Free Cancellation
Reviews
Pros: The plane was new and the seats were nice.
1 / 10
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.