Find cheap flights to Chicago from $165 - Compare and Save

1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago
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Cheap Flights to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals to Chicago

Thu, Aug 20 - Tue, Sep 1
Frontier Logo
1:17 pm - 4:00 pm
DFW
-
ORD
2h 43mnonstop
Frontier Logo
2:06 pm - 10:31 pm
ORD
-
DFW
8h 25m
1 stop
$165Frontier
Wed, Aug 12 - Wed, Aug 19
Frontier Logo
1:17 pm - 4:00 pm
DFW
-
ORD
2h 43mnonstop
Frontier Logo
2:06 pm - 10:31 pm
ORD
-
DFW
8h 25m
1 stop
$166Frontier
Sat, Aug 22 - Wed, Aug 26
American Airlines Logo
9:46 pm - 11:42 pm
LGA
-
ORD
2h 56mnonstop
American Airlines Logo
3:04 pm - 6:22 pm
ORD
-
LGA
2h 18mnonstop
$186American Airlines
Sat, Jul 18 - Tue, Jul 28
United Airlines Logo
7:21 am - 9:00 am
LGA
-
ORD
2h 39mnonstop
United Airlines Logo
7:00 am - 10:17 am
ORD
-
LGA
2h 17mnonstop
$187United Airlines
Tue, Aug 4 - Sat, Aug 8
American Airlines Logo
9:29 pm - 11:30 pm
LGA
-
ORD
3h 01mnonstop
American Airlines Logo
6:57 pm - 10:17 pm
ORD
-
LGA
2h 20mnonstop
$188American Airlines
Mon, Sep 14 - Wed, Sep 16
United Airlines Logo
7:20 am - 9:00 am
LGA
-
ORD
2h 40mnonstop
United Airlines Logo
6:00 am - 9:13 am
ORD
-
LGA
2h 13mnonstop
$192United Airlines
Sat, Sep 19 - Sun, Sep 27
Delta Logo
7:50 am - 9:42 am
JFK
-
ORD
2h 52mnonstop
Delta Logo
6:00 am - 9:21 am
ORD
-
JFK
2h 21mnonstop
$192Delta
Wed, Aug 5 - Sat, Aug 8
Delta Logo
6:00 am - 10:42 am
EWR
-
ORD
5h 42m
1 stop
Delta Logo
5:18 pm - 11:25 pm
ORD
-
EWR
5h 07m
1 stop
$207Delta
Mon, Sep 28 - Tue, Sep 29
Alaska Airlines Logo
8:25 am - 7:21 pm
SFO
-
ORD
8h 56m
1 stop
Alaska Airlines Logo
7:20 am - 1:00 pm
ORD
-
SFO
7h 40m
1 stop
$315Alaska Airlines
Fri, Oct 9 - Tue, Oct 13
Alaska Airlines Logo
10:35 am - 11:59 pm
SFO
-
ORD
11h 24m
1 stop
Alaska Airlines Logo
7:16 pm - 9:39 am
ORD
-
SFO
16h 23m
1 stop
$321Alaska Airlines