$59 Find Cheap Flights from Wisconsin to Chicago - Compare and Save

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 9/11. 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, Aug 18 - Tue, Aug 25
Delta Logo
6:57 am - 8:39 am
MSP
-
MDW
1h 42mnonstop
Delta Logo
9:59 am - 11:42 am
MDW
-
MSP
1h 43mnonstop
$117Delta
Sat, Sep 5 - Sun, Sep 6
Delta Logo
8:10 pm - 9:47 pm
MSP
-
ORD
1h 37mnonstop
Delta Logo
6:00 am - 7:30 am
ORD
-
MSP
1h 30mnonstop
$117Delta
Mon, Nov 2 - Mon, Nov 9
United Airlines Logo
8:00 am - 9:44 am
MSP
-
ORD
1h 44mnonstop
United Airlines Logo
6:00 pm - 7:39 pm
ORD
-
MSP
1h 39mnonstop
$119United Airlines
Sat, Sep 5 - Sat, Sep 12
Southwest Logo
6:00 am - 1:20 pm
MSP
-
MDW
7h 20m
2 stops
Southwest Logo
9:05 am - 2:25 pm
MDW
-
MSP
5h 20m
1 stop
$122Southwest
Thu, Sep 3 - Sun, Sep 6
Southwest Logo
2:05 pm - 10:20 pm
MSP
-
MDW
8h 15m
1 stop
Southwest Logo
8:40 am - 10:20 am
MDW
-
MSP
1h 40mnonstop
$123Southwest
Thu, Aug 13 - Mon, Aug 17
United Airlines Logo
9:45 am - 11:29 am
MSP
-
ORD
1h 44mnonstop
United Airlines Logo
6:59 am - 8:39 am
ORD
-
MSP
1h 40mnonstop
$131United Airlines
Tue, Aug 18 - Thu, Aug 20
Sun Country Air Logo
10:30 am - 12:17 pm
MSP
-
ORD
1h 47mnonstop
Sun Country Air Logo
5:42 pm - 7:18 pm
ORD
-
MSP
1h 36mnonstop
$138Sun Country Air
Thu, Aug 13 - Mon, Aug 17
Sun Country Air Logo
3:40 pm - 5:29 pm
MSP
-
ORD
1h 49mnonstop
Sun Country Air Logo
6:59 am - 8:39 am
ORD
-
MSP
1h 40mnonstop
$146Sun Country Air
Fri, Sep 11 - Tue, Sep 15
American Airlines Logo
1:18 pm - 2:39 pm
MKE
-
ORD
1h 21mnonstop
American Airlines Logo
8:51 pm - 9:54 pm
ORD
-
MKE
1h 03mnonstop
$181American Airlines
Tue, Sep 1 - Tue, Sep 1
American Airlines Logo
5:00 am - 6:14 am
MKE
-
ORD
1h 14mnonstop
American Airlines Logo
10:00 am - 10:57 am
ORD
-
MKE
0h 57mnonstop
$186American Airlines
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Good to know

Low season

June

Cheapest flight

$59
Best time to beat the crowds with an average 26% drop in price.
Most popular time to fly and prices are also 18% 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.

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 $429
Business Class flights to Chicagofrom $595
Premium Economy Class flights to Chicagofrom $676
Economy Class flights to Chicagofrom $253