$72 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 2/28. 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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Everything you should know

Cheapest round-trip
$118
Overall average: $240
Sun Country Air
Sat 3/14Sun 3/22
MSP - ORD • Non-stop
Cheapest one-way
$72
Typical prices: $118-$339
Southwest
Sat 2/28
MSP - MDW • Non-stop
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Flight Deals
Useful Info
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

Sat, Mar 14 - Sun, Mar 22
Sun Country Air Logo
7:18 pm - 8:50 pm
MSP
-
ORD
1h 32mnonstop
Sun Country Air Logo
7:30 am - 9:13 am
ORD
-
MSP
1h 43mnonstop
$118Sun Country Air
Tue, Feb 24 - Tue, Mar 3
Southwest Logo
2:30 pm - 7:55 pm
MSP
-
MDW
5h 25m
1 stop
Southwest Logo
1:50 pm - 9:50 pm
MDW
-
MSP
8h 00m
1 stop
$122Southwest
Fri, Feb 20 - Sun, Feb 22
Sun Country Air Logo
10:54 am - 12:27 pm
MSP
-
ORD
1h 33mnonstop
Sun Country Air Logo
7:05 am - 8:48 am
ORD
-
MSP
1h 43mnonstop
$128Sun Country Air
Mon, Apr 27 - Thu, May 14
Multiple Airlines Logo
3:40 pm - 12:52 am
MSP
-
ORD
9h 12m
1 stop
Multiple Airlines Logo
8:06 pm - 9:48 pm
ORD
-
MSP
1h 42mnonstop
$144Multiple Airlines
Thu, Feb 19 - Sun, Feb 22
Multiple Airlines Logo
8:27 pm - 8:12 pm
MSP
-
ORD
23h 45m
1 stop
Multiple Airlines Logo
7:05 am - 8:48 am
ORD
-
MSP
1h 43mnonstop
$147Multiple Airlines
Tue, Apr 7 - Sat, Apr 11
Frontier Logo
11:55 am - 8:07 pm
MSP
-
MDW
8h 12m
1 stop
Frontier Logo
6:00 am - 3:14 pm
MDW
-
MSP
9h 14m
1 stop
$160Frontier
Tue, Feb 24 - Tue, Mar 3
United Airlines Logo
6:00 am - 7:06 am
MKE
-
ORD
1h 06mnonstop
United Airlines Logo
8:39 pm - 9:44 pm
ORD
-
MKE
1h 05mnonstop
$177United Airlines
Sat, Mar 14 - Sat, Mar 21
United Airlines Logo
3:07 pm - 4:53 pm
DLH
-
ORD
1h 46mnonstop
United Airlines Logo
8:50 am - 10:43 am
ORD
-
DLH
1h 53mnonstop
$179United Airlines
Wed, Apr 8 - Fri, Apr 17
American Airlines Logo
5:18 pm - 6:49 pm
GRB
-
ORD
1h 31mnonstop
American Airlines Logo
3:38 pm - 4:48 pm
ORD
-
GRB
1h 10mnonstop
$179American Airlines
Wed, Feb 18 - Mon, Feb 23
American Airlines Logo
8:24 pm - 9:31 pm
MSN
-
ORD
1h 07mnonstop
American Airlines Logo
8:05 am - 9:11 am
ORD
-
MSN
1h 06mnonstop
$179American Airlines
Useful Info

Good to know

Low seasonJune
Cheapest flight$72
Best time to beat the crowds with an average 24% drop in price.
Most popular time to fly and prices are also 2% 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.
First Class flights to Chicagofrom $329
Business Class flights to Chicagofrom $522
Premium Economy Class flights to Chicagofrom $848
Economy Class flights to Chicagofrom $230