$49 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 4/28. 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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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

Wed, Apr 1 - Wed, Apr 8
United Airlines Logo
10:45 am - 11:54 am
MKE
-
ORD
1h 09mnonstop
United Airlines Logo
10:30 am - 11:32 am
ORD
-
MKE
1h 02mnonstop
$97United Airlines
Wed, Apr 1 - Wed, Apr 8
Southwest Logo
4:10 pm - 5:00 pm
MKE
-
MDW
0h 50mnonstop
Southwest Logo
12:20 pm - 5:15 pm
MDW
-
MKE
4h 55m
1 stop
$107Southwest
Tue, Apr 21 - Mon, Apr 27
Delta Logo
8:00 pm - 9:38 pm
MSP
-
ORD
1h 38mnonstop
Delta Logo
7:09 pm - 8:46 pm
ORD
-
MSP
1h 37mnonstop
$127Delta
Sat, Apr 18 - Sat, Apr 25
Delta Logo
6:15 pm - 7:52 pm
MSP
-
ORD
1h 37mnonstop
Delta Logo
7:07 pm - 8:44 pm
ORD
-
MSP
1h 37mnonstop
$131Delta
Fri, Apr 10 - Mon, Apr 20
Sun Country Air Logo
4:24 pm - 6:00 pm
MSP
-
ORD
1h 36mnonstop
Sun Country Air Logo
7:05 pm - 8:51 pm
ORD
-
MSP
1h 46mnonstop
$136Sun Country Air
Thu, Apr 23 - Thu, Apr 30
Sun Country Air Logo
4:42 pm - 6:18 pm
MSP
-
ORD
1h 36mnonstop
Sun Country Air Logo
8:06 pm - 9:52 pm
ORD
-
MSP
1h 46mnonstop
$137Sun Country Air
Sat, Apr 4 - Sat, Apr 11
American Airlines Logo
8:31 am - 9:42 am
MKE
-
ORD
1h 11mnonstop
American Airlines Logo
12:22 pm - 1:23 pm
ORD
-
MKE
1h 01mnonstop
$153American Airlines
Thu, Apr 16 - Sun, Apr 19
American Airlines Logo
8:11 am - 9:25 am
MKE
-
ORD
1h 14mnonstop
American Airlines Logo
6:40 am - 7:41 am
ORD
-
MKE
1h 01mnonstop
$178American Airlines
Sat, Apr 25 - Mon, Apr 27
Multiple Airlines Logo
4:30 pm - 9:47 am
MSP
-
RFD
17h 17m
1 stop
Multiple Airlines Logo
8:35 pm - 1:54 pm
RFD
-
MSP
17h 19m
1 stop
$393Multiple Airlines
Wed, Apr 22 - Mon, Apr 27
Multiple Airlines Logo
6:18 am - 9:47 am
MSP
-
RFD
27h 29m
2 stops
Multiple Airlines Logo
8:35 pm - 1:54 pm
RFD
-
MSP
17h 19m
1 stop
$406Multiple Airlines
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Good to know

Low seasonJanuary
Cheapest flight$49
Best time to beat the crowds but there is an average 8% increase in price.
Flight from Milwaukee 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.