$59 Find Cheap Flights from Wisconsin to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 5/5. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Flight Deals

Cheap Flights from Wisconsin to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Wisconsin 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 from Wisconsin to Chicago

Tue, May 5 - Tue, May 12
Southwest Logo
10:05 am - 11:35 am
MSP
-
MDW
1h 30mnonstop
Southwest Logo
7:55 am - 9:25 am
MDW
-
MSP
1h 30mnonstop
$117Southwest
Tue, May 5 - Tue, May 12
United Airlines Logo
9:57 am - 11:33 am
MSP
-
ORD
1h 36mnonstop
United Airlines Logo
2:35 pm - 4:13 pm
ORD
-
MSP
1h 38mnonstop
$117United Airlines
Wed, May 6 - Wed, May 13
American Airlines Logo
8:19 am - 10:07 am
MSP
-
ORD
1h 48mnonstop
American Airlines Logo
9:10 am - 10:54 am
ORD
-
MSP
1h 44mnonstop
$118American Airlines
Tue, May 12 - Thu, May 14
Sun Country Air Logo
10:55 am - 12:31 pm
MSP
-
ORD
1h 36mnonstop
Sun Country Air Logo
8:00 am - 9:44 am
ORD
-
MSP
1h 44mnonstop
$137Sun Country Air
Sat, Jul 4 - Tue, Jul 7
Sun Country Air Logo
3:30 pm - 5:19 pm
MSP
-
ORD
1h 49mnonstop
Sun Country Air Logo
11:55 am - 1:41 pm
ORD
-
MSP
1h 46mnonstop
$138Sun Country Air
Tue, May 12 - Sat, May 16
Multiple Airlines Logo
10:55 am - 12:31 pm
MSP
-
ORD
1h 36mnonstop
Multiple Airlines Logo
6:55 am - 1:37 pm
ORD
-
MSP
6h 42m
1 stop
$144Multiple Airlines
Thu, May 7 - Sat, May 9
Multiple Airlines Logo
5:30 pm - 7:06 pm
MSP
-
ORD
1h 36mnonstop
Multiple Airlines Logo
6:55 am - 1:37 pm
ORD
-
MSP
6h 42m
1 stop
$145Multiple Airlines
Fri, May 1 - Sat, May 2
Frontier Logo
12:36 pm - 10:26 pm
MSP
-
MDW
9h 50m
1 stop
Frontier Logo
9:14 am - 9:39 am
MDW
-
MSP
24h 25m
1 stop
$151Frontier
Tue, May 19 - Sun, May 24
American Airlines Logo
5:06 am - 6:25 am
MKE
-
ORD
1h 19mnonstop
American Airlines Logo
8:02 pm - 9:04 pm
ORD
-
MKE
1h 02mnonstop
$200American Airlines
Tue, May 12 - Wed, May 13
Frontier Logo
9:56 am - 7:55 am
MKE
-
ORD
21h 59m
2 stops
Frontier Logo
3:55 pm - 9:01 am
ORD
-
MKE
17h 06m
1 stop
$236Frontier
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Good to know

Low seasonJanuary
Cheapest flight$59
Best time to beat the crowds but there is an average 14% increase in price.
Most popular time to fly and prices are also 4% lower on average.
Flight from Minneapolis to Chicago Midway Airport

FAQs for booking flights from Wisconsin to Chicago

  • How does KAYAK find such low prices on flights from Wisconsin to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Wisconsin to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Wisconsin to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Wisconsin is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Wisconsin to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Wisconsin with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Wisconsin to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Wisconsin up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Lansing
Valparaiso
Chesterton
Schererville
Munster
Porter
Monticello
Griffith
Saint John

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Wisconsin

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.