Find Cheap Flights to Chicago

Depart
Return
1 adult
Adults
18-64
Seniors
65+
Youths
12-17
Children
2-11
Seat Infants
under 2
Lap Infants
under 2
The price shown for each flight will be the average for all passengers including any infants.
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Book cheap flights from Valparaiso Destin-Ft Walton Beach to Chicago

(Round-trip)
Depart: Fri Sep 29 2017 Return: Mon Oct 2 2017 Trip spans 4 days
American Airlines
American Airlines
VPS
ORD
4h 58m
1 stop
ORD
VPS
5h 27m
1 stop
Depart: Wed Oct 11 2017 Return: Wed Oct 18 2017 Trip spans 8 days
Delta
Delta
VPS
MDW
5h 25m
1 stop
MDW
VPS
5h 02m
1 stop
Depart: Fri Oct 20 2017 Return: Tue Oct 24 2017 Trip spans 5 days
American Airlines
American Airlines
VPS
ORD
4h 58m
1 stop
ORD
VPS
5h 04m
1 stop
Depart: Fri Oct 20 2017 Return: Tue Oct 24 2017 Trip spans 5 days
Delta
Delta
VPS
MDW
4h 45m
1 stop
MDW
VPS
5h 13m
1 stop
Depart: Fri Nov 3 2017 Return: Tue Nov 7 2017 Trip spans 5 days
American Airlines
American Airlines
VPS
ORD
6h 21m
1 stop
ORD
VPS
6h 28m
1 stop
Depart: Thu Nov 9 2017 Return: Sun Nov 12 2017 Trip spans 4 days
Delta
Delta
VPS
MDW
5h 12m
1 stop
MDW
VPS
5h 41m
1 stop
Depart: Tue Nov 14 2017 Return: Mon Nov 20 2017 Trip spans 7 days
American Airlines
American Airlines
VPS
ORD
5h 05m
1 stop
ORD
VPS
7h 23m
1 stop
Depart: Wed Oct 11 2017 Return: Wed Oct 18 2017 Trip spans 8 days
Delta
Delta
VPS
ORD
5h 59m
1 stop
ORD
VPS
4h 41m
1 stop
Depart: Thu Sep 7 2017 Return: Sat Sep 9 2017 Trip spans 3 days
American Airlines
American Airlines
VPS
ORD
4h 58m
1 stop
ORD
VPS
5h 48m
1 stop
Depart: Thu Aug 31 2017 Return: Tue Sep 5 2017 Trip spans 6 days
Delta
Delta
VPS
MDW
4h 52m
1 stop
MDW
VPS
4h 43m
1 stop
Depart: Sun Sep 3 2017 Return: Wed Sep 6 2017 Trip spans 4 days
Delta
Delta
VPS
MDW
6h 00m
1 stop
MDW
VPS
4h 08m
1 stop
Depart: Thu Aug 31 2017 Return: Mon Sep 4 2017 Trip spans 5 days
Delta
Delta
VPS
ORD
4h 24m
1 stop
ORD
VPS
6h 50m
1 stop
Depart: Fri Sep 1 2017 Return: Tue Sep 5 2017 Trip spans 5 days
Delta
Delta
VPS
MDW
7h 05m
1 stop
MDW
VPS
3h 58m
1 stop
Depart: Fri Sep 1 2017 Return: Tue Sep 5 2017 Trip spans 5 days
Delta
Delta
VPS
ORD
4h 20m
1 stop
ORD
VPS
3h 44m
1 stop
Depart: Sun Sep 10 2017 Return: Thu Sep 14 2017 Trip spans 5 days
Delta
Delta
VPS
MDW
3h 48m
1 stop
MDW
VPS
5h 19m
1 stop
Depart: Thu Aug 24 2017 Return: Sun Aug 27 2017 Trip spans 4 days
American Airlines
American Airlines
VPS
ORD
5h 04m
1 stop
ORD
VPS
4h 45m
1 stop
Depart: Thu Aug 24 2017 Return: Sun Aug 27 2017 Trip spans 4 days
Delta
Delta
VPS
MDW
3h 35m
1 stop
MDW
VPS
4h 08m
1 stop
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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Here's why:

We’re not the seller.
At KAYAK we don’t set the prices, so it’s not possible for us to guarantee what other companies are selling.

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Our service lets you quickly and easily compare results from hundreds of travel sites at once. In this sense, KAYAK is a search engine and we can't guarantee prices we find.

Why aren’t prices accurate 100% of the time?
Prices on airline seats, hotel rooms and car rentals can change frequently. Several people may also be trying to buy the same travel option simultaneously. As a result, you may find, on occasion, that certain prices are no longer available.

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Airports
Origin

Valparaiso
$233
Destination

Chicago
only $233
only $236