Flights from Boston to Chicago

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Boston to Chicago flight comparison made easy

Below you can see the best fares for your 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
Quickest
Cheapest
American Airlines
American Airlines
BOS
2:00 am
Boston Logan Intl airport
2h 50m
3:50 am
ORD
Chicago O'Hare Intl airport
American Airlines
ORD
2:45 am
Chicago O'Hare Intl airport
2h 16m
6:01 am
BOS
Boston Logan Intl airport
105 USD
United Airlines
United Airlines
BOS
3:15 am
Boston Logan Intl airport
2h 46m
5:01 am
ORD
Chicago O'Hare Intl airport
United Airlines
ORD
1:00 am
Chicago O'Hare Intl airport
2h 18m
4:18 am
BOS
Boston Logan Intl airport
105 USD
American Airlines
American Airlines
BOS
5:00 am
Boston Logan Intl airport
2h 55m
6:55 am
ORD
Chicago O'Hare Intl airport
American Airlines
ORD
1:00 am
Chicago O'Hare Intl airport
2h 18m
4:18 am
BOS
Boston Logan Intl airport
105 USD
American Airlines
American Airlines
BOS
1:00 am
Boston Logan Intl airport
2h 44m
2:44 am
ORD
Chicago O'Hare Intl airport
American Airlines
ORD
1:00 am
Chicago O'Hare Intl airport
2h 18m
4:18 am
BOS
Boston Logan Intl airport
105 USD
United Airlines
United Airlines
BOS
3:15 am
Boston Logan Intl airport
2h 46m
5:01 am
ORD
Chicago O'Hare Intl airport
United Airlines
ORD
1:00 am
Chicago O'Hare Intl airport
2h 18m
4:18 am
BOS
Boston Logan Intl airport
105 USD
United Airlines
United Airlines
BOS
4:25 am
Boston Logan Intl airport
2h 46m
6:11 am
ORD
Chicago O'Hare Intl airport
United Airlines
ORD
5:19 pm
Chicago O'Hare Intl airport
2h 18m
8:37 pm
BOS
Boston Logan Intl airport
105 USD

How to get the cheapest flight 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 for your trip
CHEAPEST MONTH TO FLY
September
The cheapest time of year to fly to Chicago from Boston is September. Most expensive is November
CHEAPEST DAY TO FLY
Tuesday
The cheapest day of the week is typically Tuesday. The most expensive is typically Friday
CHEAPEST TIME TO FLY
in the Morning
Boston to Chicago flights are approximately 23% more expensive in the Afternoon than in the Morning
CHEAPEST AIRLINE
Spirit Airlines
Spirit Airlines, JetBlue, and Delta are the most popular carriers operating from Boston to Chicago
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
CHEAPEST TIME TO BOOK
30 days before
The cheapest time to buy a flight from Boston to Chicago is approximately 30 days to departure
60
Days before departure
0

Flight information for Boston to Chicago

Find info about flight duration, direct flights, and airports for your flight from Boston to Chicago
Fastest flight time
2h 42m
The fastest flight from Boston to Chicago takes 2h 42m.
Direct flights
Every day
Direct flights go from Boston to Chicago every day.
Airports in Chicago
3 airports
There are 3 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW), Chicago Greater Rockford (RFD)

Alternative routes for Boston to Chicago

Compare alternative flights to and from nearby airports and cities to discover the best prices and most convenient flight times

Cost comparison between Boston and Chicago

Compare the costs of everyday items in Boston and Chicago
Food
Inexpensive restaurant
15 USD
Boston
15 USD
Chicago
Fast food
McDonald's meal
8 USD
Boston
6.97 USD
Chicago
Soft drink
0.33 liter
1.88 USD
Boston
1.78 USD
Chicago
Coffee
Cappuccino
4 USD
Boston
4.13 USD
Chicago
Public transport
One-way ticket
2.51 USD
Boston
2.49 USD
Chicago

Flights from Boston to:

Flights to Chicago from:

  • Boston Logan Intl
  • Massachusetts
  • United States
  • North America