Cheap flights from Boston to Chicago

Round-trip
Economy
Boston (BOS)
Chicago (CHI)
Sun 12/20
Sun 12/27
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 $48 The best flight deal from Boston to Chicago found on momondo in the last 72 hours is $48
Fastest flight time 2h 43m The fastest flight from Boston to Chicago takes 2h 43m.
Direct flights Tu, We, Th, Sa and Su Direct flights go from Boston to Chicago on Tuesday, Wednesday, Thursday, Saturday and Sunday. 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 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 fly to Chicago?
Saturday
The cheapest day of the week is typically Saturday. The most expensive is typically Sunday
When is the cheapest time to fly 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?
Spirit Airlines
Spirit Airlines, Envoy Air, and Delta are the most popular carriers operating from Boston to Chicago
What is the cheapest 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
When is the cheapest time to book a flight to Chicago?
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
Cheapest
Best
Quickest
Spirit Airlines
Dec 5
BOS
Boston Logan Intl
12h 14m
1 stop
ORD
Chicago O'Hare Intl
Jan 16
ORD
Chicago O'Hare Intl
12h 02m
1 stop
BOS
Boston Logan Intl
Frontier
Feb 4
BOS
Boston Logan Intl
10h 48m
1 stop
ORD
Chicago O'Hare Intl
Feb 7
ORD
Chicago O'Hare Intl
11h 07m
1 stop
BOS
Boston Logan Intl
Multiple Airlines
Jan 16
BOS
Boston Logan Intl
13h 08m
1 stop
ORD
Chicago O'Hare Intl
Jan 19
ORD
Chicago O'Hare Intl
2h 16m
BOS
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 and Frontier
Cheapest
Best
Quickest
Spirit Airlines
Dec 18
BOS
Boston Logan Intl
8h 12m
1 stop
ORD
Chicago O'Hare Intl
Frontier
Jan 19
BOS
Boston Logan Intl
8h 55m
1 stop
ORD
Chicago O'Hare Intl
JetBlue
Jan 15
BOS
Boston Logan Intl
3h 03m
ORD
Chicago O'Hare Intl

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

Airlines such as JetBlue, Southwest, and 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.


Flights from Boston to:

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