Cheap flights from Boston to Chicago

Round-trip
Economy
Boston (BOS)
Chicago (CHI)
Mon 7/6
Mon 7/13
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 $32 The best flight deal from Boston to Chicago found on momondo in the last 72 hours is $32
Fastest flight time 2h 33m The fastest flight from Boston to Chicago takes 2h 33m.
Direct flights None There are no direct flights from Boston to Chicago. Popular non-direct routes for this connection are Boston Logan Intl - Chicago O'Hare Intl and Boston Logan Intl - Chicago Midway.
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?
September
The cheapest time of year to fly to Chicago from Boston is September. Most expensive is July
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?
Frontier
Frontier, Sun Country Air, and Spirit Airlines 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?
56 days before
The cheapest time to buy a flight from Boston to Chicago is approximately 56 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
Jul 8
BOS
Boston Logan Intl
2h 55m
ORD
Chicago O'Hare Intl
Jul 15
ORD
Chicago O'Hare Intl
2h 27m
BOS
Boston Logan Intl
Multiple Airlines
Jul 8
BOS
Boston Logan Intl
2h 55m
ORD
Chicago O'Hare Intl
Jul 12
ORD
Chicago O'Hare Intl
2h 34m
BOS
Boston Logan Intl
Spirit Airlines
Aug 20
BOS
Boston Logan Intl
2h 55m
ORD
Chicago O'Hare Intl
Aug 25
ORD
Chicago O'Hare Intl
2h 27m
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
Cheapest
Best
Quickest
Spirit Airlines
Jul 8
BOS
Boston Logan Intl
2h 55m
ORD
Chicago O'Hare Intl
Delta
Jul 14
BOS
Boston Logan Intl
2h 55m
ORD
Chicago O'Hare Intl
Spirit Airlines
Jul 14
BOS
Boston Logan Intl
2h 55m
ORD
Chicago O'Hare Intl

Flights from Boston to:

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Economy
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  • First