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When is the best time to fly to Chicago?

$2,670
$2,180
$1,700
$1,213
Price
$1,213 - $2,411

When is the best time to fly to Chicago?

In general when looking for the cheapest flight to Chicago, try to book your flight during the month of August for the best deal.

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

In general, most flyers find the cheapest time to book a flight to Chicago is about 20 days prior.

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

Most of our users find that booking their departure to Chicago on a Tuesday is the cheapest. Conversely, departing on a Saturday seems to be the most expensive.

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

Generally, when visiting Chicago, morning flights represent the best value. afternoon flights are likely to have higher prices.


Chicago flight deals found on momondo

Check out some of the best fares to Chicago found recently by users on momondo
Quickest
Cheapest
Air New Zealand
Air New Zealand
11 Mar.
SYD
Sydney Kingsford Smith airport
21h 15m
1 Stop
ORD
Chicago O'Hare Intl airport
Air New Zealand
27 Mar.
ORD
Chicago O'Hare Intl airport
22h 25m
1 Stop
SYD
Sydney Kingsford Smith airport
$1,080
Air New Zealand
Air New Zealand
12 Jul.
SYD
Sydney Kingsford Smith airport
21h 40m
1 Stop
ORD
Chicago O'Hare Intl airport
Air New Zealand
07 Aug.
ORD
Chicago O'Hare Intl airport
22h 20m
1 Stop
SYD
Sydney Kingsford Smith airport
$1,102
China Eastern
China Eastern
08 Feb.
SYD
Sydney Kingsford Smith airport
41h 45m
1 Stop
ORD
Chicago O'Hare Intl airport
China Eastern
22 Feb.
ORD
Chicago O'Hare Intl airport
27h 10m
1 Stop
SYD
Sydney Kingsford Smith airport
$1,105
Air New Zealand
Air New Zealand
30 May
SYD
Sydney Kingsford Smith airport
41h 50m
1 Stop
ORD
Chicago O'Hare Intl airport
Air New Zealand
07 Jun.
ORD
Chicago O'Hare Intl airport
22h 20m
1 Stop
SYD
Sydney Kingsford Smith airport
$1,121
Air New Zealand
Air New Zealand
23 Apr.
SYD
Sydney Kingsford Smith airport
28h 06m
2 Stops
ORD
Chicago O'Hare Intl airport
Air New Zealand
24 May
ORD
Chicago O'Hare Intl airport
22h 20m
1 Stop
SYD
Sydney Kingsford Smith airport
$1,140
Qantas Airways
Qantas Airways
03 Jun.
MEL
Melbourne airport
21h 20m
1 Stop
ORD
Chicago O'Hare Intl airport
Qantas Airways
08 Jun.
ORD
Chicago O'Hare Intl airport
22h 50m
1 Stop
MEL
Melbourne airport
$1,175
Air New Zealand
Air New Zealand
24 Jan.
SYD
Sydney Kingsford Smith airport
19h 25m
1 Stop
ORD
Chicago O'Hare Intl airport
Air New Zealand
21 Feb.
ORD
Chicago O'Hare Intl airport
22h 20m
1 Stop
SYD
Sydney Kingsford Smith airport
$1,621
Air New Zealand
Air New Zealand
11 Mar.
SYD
Sydney Kingsford Smith airport
21h 15m
1 Stop
ORD
Chicago O'Hare Intl airport
Air New Zealand
27 Mar.
ORD
Chicago O'Hare Intl airport
22h 25m
1 Stop
SYD
Sydney Kingsford Smith airport
$1,080
Air New Zealand
Air New Zealand
12 Jul.
SYD
Sydney Kingsford Smith airport
21h 40m
1 Stop
ORD
Chicago O'Hare Intl airport
Air New Zealand
07 Aug.
ORD
Chicago O'Hare Intl airport
22h 20m
1 Stop
SYD
Sydney Kingsford Smith airport
$1,102
Qantas Airways
Qantas Airways
03 Jun.
MEL
Melbourne airport
21h 20m
1 Stop
ORD
Chicago O'Hare Intl airport
Qantas Airways
08 Jun.
ORD
Chicago O'Hare Intl airport
22h 50m
1 Stop
MEL
Melbourne airport
$1,175
Air New Zealand
Air New Zealand
23 Apr.
SYD
Sydney Kingsford Smith airport
28h 06m
2 Stops
ORD
Chicago O'Hare Intl airport
Air New Zealand
24 May
ORD
Chicago O'Hare Intl airport
22h 20m
1 Stop
SYD
Sydney Kingsford Smith airport
$1,140
Delta
Delta
11 Mar.
SYD
Sydney Kingsford Smith airport
23h 43m
2 Stops
MDW
Chicago Midway airport
Delta
27 Mar.
MDW
Chicago Midway airport
28h 28m
2 Stops
SYD
Sydney Kingsford Smith airport
$1,535

Which airlines operate flights to Chicago?


Airports near Chicago

Below you will find all the airports in Chicago along with their distance from the city centre
Chicago Midway
13 km from city centre
Chicago O'Hare Intl
24 km from city centre
Chicago Greater Rockford
126 km from city centre

Popular routes to Chicago

Most frequently searched flights to Chicago along with the cheapest price and shortest flight duration
Newark to Chicago Flights
Fastest flight time
2h 31m
Cheapest price
$272
Los Angeles to Chicago Flights
Fastest flight time
4h 06m
Cheapest price
$272
Sydney to Chicago Flights
Fastest flight time
19h 25m
Cheapest price
$1,060
Brisbane to Chicago Flights
Fastest flight time
16h 10m
Cheapest price
$1,137
Melbourne to Chicago Flights
Fastest flight time
20h 55m
Cheapest price
$1,143
Perth to Chicago Flights
Fastest flight time
26h 50m
Cheapest price
$1,327
Adelaide to Chicago Flights
Fastest flight time
27h 23m
Cheapest price
$1,362
Cairns to Chicago Flights
Fastest flight time
26h 15m
Cheapest price
$1,442
Townsville to Chicago Flights
Fastest flight time
34h 10m
Cheapest price
$1,554
Coolangatta to Chicago Flights
Fastest flight time
25h 15m
Cheapest price
$1,855
View more

Start planning your trip to Chicago