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Cheap flights from Chicago to Boston
Round-trip
Economy
Flight information for Chicago to Boston
(CHI to BOS)
Find info about flight duration, direct flights, and airports for your flight from Chicago to Boston
| Best Price Found | $52 | The best flight deal from Chicago to Boston found on momondo in the last 72 hours is $52 |
| Fastest flight time | 2h 21m | The fastest flight from Chicago to Boston takes 2h 21m |
| Direct flights | Mo, Tu, We, Fr, Sa and Su | Direct flights go from Chicago to Boston on Monday, Tuesday, Wednesday, Friday, Saturday and Sunday. The only airline offering direct flights is American Airlines. |
| Airports in Boston | 1 airport | There is 1 airport near Boston: Boston Logan Intl (BOS) |
How to get the cheapest flight ticket from Chicago to Boston
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 Chicago to Boston?
August
The cheapest time of year to fly to Boston from Chicago is August. Most expensive is December
What is the cheapest day to depart Chicago for Boston?
Wednesday
The cheapest day of the week is typically Wednesday. The most expensive is typically Sunday
When is the cheapest time to fly from Chicago to Boston?
at noon
Chicago to Boston flights are approximately 32% more expensive in the afternoon than at noon
What is the cheapest airline that flies to Boston from Chicago?
Spirit Airlines
Spirit Airlines, Delta, and Envoy Air are the most popular carriers operating from Chicago to Boston
What is the cheapest Chicago to Boston flight route?
Chicago O'Hare Intl - Boston Logan Intl
Fly from Chicago O'Hare Intl to Boston Logan Intl for the best Chicago - Boston flight prices
How far in advance should you book Chicago to Boston flights?
5 days before
The cheapest time to buy a flight from Chicago to Boston is approximately 5 days to departure
60
Days before departure
0
Easily compare round-trip flights from Chicago to Boston
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 Chicago to Boston by changing tabs
Spirit Airlines![Spirit Airlines]()
Oct 2![Spirit Airlines]()
Oct 6
ORD5:00 amChicago O'Hare Intl
2h 18m
BOS7:18 amBoston Logan Intl
BOS5:53 pmBoston Logan Intl
2h 33m
ORD8:26 pmChicago O'Hare Intl
Spirit Airlines![Spirit Airlines]()
Sep 14![Spirit Airlines]()
Sep 18
ORD5:00 amChicago O'Hare Intl
2h 18m
BOS7:18 amBoston Logan Intl
BOS5:53 pmBoston Logan Intl
2h 33m
ORD8:26 pmChicago O'Hare Intl
Find the cheapest one-way flights from Chicago to Boston
If you're looking for one-way flights from Chicago to Boston, view some of our deals below provided by Spirit Airlines
Best airlines flying from Chicago to Boston
Compare and see reviews for airlines that fly from Chicago to Boston with momondo
AirlineFree CancellationPrice
PriceFrom $48
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 $54
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 $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 $76
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 $76
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 $189
Free Cancellation
Reviews
Pros: The plane was new and the seats were nice.
1 / 10
Are airlines flying from Chicago to Boston Logan Intl offering flexible cancellation due to COVID-19?
Due to the global impact of COVID-19, some of our airline partners operating flights from Chicago to Boston Logan Intl, such as American Airlines, United Airlines, and Spirit Airlines may have put in place flexible cancellation policies. Use our site to search for all of the airlines offering this flexibility to you.