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When is the best time to fly to Chicago?

$350
$290
$220
$160
Price
$160 - $300

When is the best time to fly to Chicago?

Most travelers find the cheapest round-trip airfare to Chicago when booking during the month of February.

When is the best time to book a flight to Chicago?

From most locations, booking your flights to Chicago around 57 days prior to your departure date finds the best deals.

What is the cheapest day to depart on your flight to Chicago?

On average, the cheapest flights to Chicago are found when departing on a Tuesday. Try to avoid departing on a Sunday, as this is usually the most expensive day.

What is the cheapest time of day to fly to Chicago?

In general, when looking for the cheapest flight to Chicago, our data indicates that evening flights are the most cost-effective. afternoon flights tend to be the most expensive.


Chicago flight deals found on momondo

Check out some of the best fares to Chicago found recently by users on momondo
Quickest
Cheapest
Spirit Airlines
Spirit Airlines
30 Jan
DFW
Dallas/Fort Worth airport
2h 23m
ORD
Chicago O'Hare Intl airport
Spirit Airlines
04 Feb
ORD
Chicago O'Hare Intl airport
2h 35m
DFW
Dallas/Fort Worth airport
$65
Spirit Airlines
Spirit Airlines
19 Feb
BWI
Baltimore/Washington airport
2h 17m
ORD
Chicago O'Hare Intl airport
Spirit Airlines
26 Feb
ORD
Chicago O'Hare Intl airport
1h 54m
BWI
Baltimore/Washington airport
$65
Spirit Airlines
Spirit Airlines
29 Feb
LGA
New York LaGuardia airport
2h 50m
ORD
Chicago O'Hare Intl airport
Spirit Airlines
03 Mar
ORD
Chicago O'Hare Intl airport
2h 11m
LGA
New York LaGuardia airport
$69
Spirit Airlines
Spirit Airlines
12 May
BOS
Boston Logan Intl airport
2h 53m
ORD
Chicago O'Hare Intl airport
Spirit Airlines
19 May
ORD
Chicago O'Hare Intl airport
2h 31m
BOS
Boston Logan Intl airport
$75
Spirit Airlines
Spirit Airlines
04 Mar
DFW
Dallas/Fort Worth airport
2h 25m
ORD
Chicago O'Hare Intl airport
Spirit Airlines
10 Mar
ORD
Chicago O'Hare Intl airport
2h 38m
DFW
Dallas/Fort Worth airport
$76
Spirit Airlines
Spirit Airlines
29 Apr
BOS
Boston Logan Intl airport
2h 53m
ORD
Chicago O'Hare Intl airport
Spirit Airlines
05 May
ORD
Chicago O'Hare Intl airport
2h 31m
BOS
Boston Logan Intl airport
$76
Spirit Airlines
Spirit Airlines
19 Feb
BWI
Baltimore/Washington airport
2h 17m
ORD
Chicago O'Hare Intl airport
Spirit Airlines
26 Feb
ORD
Chicago O'Hare Intl airport
1h 54m
BWI
Baltimore/Washington airport
$65
American Airlines
American Airlines
05 May
EWR
Newark airport
2h 36m
ORD
Chicago O'Hare Intl airport
American Airlines
06 May
ORD
Chicago O'Hare Intl airport
2h 04m
EWR
Newark airport
$149
Spirit Airlines
Spirit Airlines
30 Jan
DFW
Dallas/Fort Worth airport
2h 23m
ORD
Chicago O'Hare Intl airport
Spirit Airlines
04 Feb
ORD
Chicago O'Hare Intl airport
2h 35m
DFW
Dallas/Fort Worth airport
$65
Spirit Airlines
Spirit Airlines
29 Feb
LGA
New York LaGuardia airport
2h 50m
ORD
Chicago O'Hare Intl airport
Spirit Airlines
03 Mar
ORD
Chicago O'Hare Intl airport
2h 11m
LGA
New York LaGuardia airport
$69
JetBlue
JetBlue
06 Feb
JFK
New York John F Kennedy Intl airport
2h 49m
ORD
Chicago O'Hare Intl airport
JetBlue
07 Feb
ORD
Chicago O'Hare Intl airport
2h 14m
JFK
New York John F Kennedy Intl airport
$177
Spirit Airlines
Spirit Airlines
04 Mar
DFW
Dallas/Fort Worth airport
2h 25m
ORD
Chicago O'Hare Intl airport
Spirit Airlines
10 Mar
ORD
Chicago O'Hare Intl airport
2h 38m
DFW
Dallas/Fort Worth airport
$76

Which is the cheapest airline for flights to Chicago?

Here you can see a selection of the most popular and cheapest airlines for your flight to Chicago

Airports near Chicago

Below you will find all the airports in Chicago along with the distance from the city center
Chicago Midway
8 mi from city center
Chicago O'Hare Intl
15 mi from city center
Chicago Greater Rockford
78 mi from city center

Popular routes to Chicago

Most frequently searched flights to Chicago along with the cheapest price and shortest flight duration
Tampa to Chicago Flights
Fastest flight time
2h 50m
Cheapest price
$61
Orlando to Chicago Flights
Fastest flight time
2h 50m
Cheapest price
$61
Phoenix to Chicago Flights
Fastest flight time
3h 19m
Cheapest price
$62
Miami to Chicago Flights
Fastest flight time
3h 21m
Cheapest price
$63
Denver to Chicago Flights
Fastest flight time
2h 18m
Cheapest price
$64
Baltimore to Chicago Flights
Fastest flight time
2h 05m
Cheapest price
$65
Dallas to Chicago Flights
Fastest flight time
2h 14m
Cheapest price
$65
Atlanta to Chicago Flights
Fastest flight time
1h 55m
Cheapest price
$65
Houston to Chicago Flights
Fastest flight time
2h 29m
Cheapest price
$65
Austin to Chicago Flights
Fastest flight time
2h 41m
Cheapest price
$65
New York to Chicago Flights
Fastest flight time
2h 35m
Cheapest price
$69
Fort Lauderdale to Chicago Flights
Fastest flight time
3h 18m
Cheapest price
$69
Fort Myers to Chicago Flights
Fastest flight time
3h 07m
Cheapest price
$73
Boston to Chicago Flights
Fastest flight time
2h 41m
Cheapest price
$75
San Diego to Chicago Flights
Fastest flight time
4h 02m
Cheapest price
$76
New Orleans to Chicago Flights
Fastest flight time
2h 29m
Cheapest price
$76
Las Vegas to Chicago Flights
Fastest flight time
3h 27m
Cheapest price
$91
Charlotte to Chicago Flights
Fastest flight time
1h 58m
Cheapest price
$94
Los Angeles to Chicago Flights
Fastest flight time
3h 47m
Cheapest price
$95
Minneapolis to Chicago Flights
Fastest flight time
1h 31m
Cheapest price
$97
View more

Start planning your trip to Chicago