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Cheap flights from Wisconsin to Chicago from $59

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Wisconsin to Chicago departing on 4/15. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Wisconsin to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
7:00 am - 8:46 am
MSP
-
MDW
1h 46mnonstop
Delta Logo
2:12 pm - 3:55 pm
MDW
-
MSP
1h 43mnonstop
$117Delta
Wed, Apr 15 - Tue, Apr 21
Delta Logo
6:05 pm - 7:43 pm
MSP
-
ORD
1h 38mnonstop
Delta Logo
9:30 am - 11:04 am
ORD
-
MSP
1h 34mnonstop
$117Delta
Tue, Jun 9 - Wed, Jun 10
Southwest Logo
3:15 pm - 4:50 pm
MSP
-
MDW
1h 35mnonstop
Southwest Logo
4:40 pm - 10:30 pm
MDW
-
MSP
5h 50m
1 stop
$127Southwest
Tue, Apr 14 - Wed, Apr 15
Southwest Logo
8:40 am - 4:35 pm
MSP
-
MDW
7h 55m
2 stops
Southwest Logo
6:20 pm - 7:50 pm
MDW
-
MSP
1h 30mnonstop
$132Southwest
Tue, Apr 14 - Wed, Apr 15
Sun Country Air Logo
4:42 pm - 6:18 pm
MSP
-
ORD
1h 36mnonstop
Sun Country Air Logo
7:35 pm - 9:21 pm
ORD
-
MSP
1h 46mnonstop
$136Sun Country Air
Thu, Apr 23 - Fri, Apr 24
Sun Country Air Logo
5:18 pm - 6:54 pm
MSP
-
ORD
1h 36mnonstop
Sun Country Air Logo
7:20 am - 9:06 am
ORD
-
MSP
1h 46mnonstop
$137Sun Country Air
Thu, Apr 16 - Sun, Apr 19
Sun Country Air Logo
5:18 pm - 6:54 pm
MSP
-
ORD
1h 36mnonstop
Sun Country Air Logo
7:20 am - 9:06 am
ORD
-
MSP
1h 46mnonstop
$138Sun Country Air
Thu, Apr 16 - Sun, Apr 19
Frontier Logo
11:57 am - 12:52 am
MSP
-
ORD
12h 55m
1 stop
Frontier Logo
9:42 pm - 9:19 am
ORD
-
MSP
11h 37m
1 stop
$140Frontier
Fri, May 1 - Wed, May 6
United Airlines Logo
7:41 pm - 8:50 pm
MKE
-
ORD
1h 09mnonstop
United Airlines Logo
10:30 am - 11:32 am
ORD
-
MKE
1h 02mnonstop
$143United Airlines
Tue, Apr 21 - Tue, Apr 28
United Airlines Logo
8:00 am - 9:37 am
MSP
-
ORD
1h 37mnonstop
United Airlines Logo
11:00 pm - 12:38 am
ORD
-
MSP
1h 38mnonstop
$147United Airlines
Sat, May 2 - Wed, May 6

Sun Country Air flights from Wisconsin to Chicago

Our best Sun Country Air deals on Wisconsin to Chicago flight tickets
Sun Country Air
Apr 23
MSP4:42 pmMinneapolis St Paul
1h 36m
ORD6:18 pmChicago O'Hare Intl
Apr 24
ORD7:35 pmChicago O'Hare Intl
1h 46m
MSP9:21 pmMinneapolis St Paul
$136
Sun Country Air
Apr 16
MSP5:18 pmMinneapolis St Paul
1h 36m
ORD6:54 pmChicago O'Hare Intl
Apr 19
ORD7:20 amChicago O'Hare Intl
1h 46m
MSP9:06 amMinneapolis St Paul
$137
Sun Country Air
Apr 16
MSP5:18 pmMinneapolis St Paul
1h 36m
ORD6:54 pmChicago O'Hare Intl
Apr 19
ORD7:20 amChicago O'Hare Intl
1h 46m
MSP9:06 amMinneapolis St Paul
$138

United Airlines flights from Wisconsin to Chicago

Our best United Airlines deals on Wisconsin to Chicago flight tickets
United Airlines
Apr 21
MKE7:41 pmMilwaukee-Mitchell
1h 09m
ORD8:50 pmChicago O'Hare Intl
Apr 28
ORD10:30 amChicago O'Hare Intl
1h 02m
MKE11:32 amMilwaukee-Mitchell
$143
United Airlines
Apr 14
MKE7:41 pmMilwaukee-Mitchell
1h 09m
ORD8:50 pmChicago O'Hare Intl
Apr 18
ORD8:15 pmChicago O'Hare Intl
1h 08m
MKE9:23 pmMilwaukee-Mitchell
$157
United Airlines
Jun 11
EAU2:40 pmEau Claire
1h 27m
ORD4:07 pmChicago O'Hare Intl
Jun 15
ORD12:35 pmChicago O'Hare Intl
1h 30m
EAU2:05 pmEau Claire
$180

momondo Fare Finder

 
Customize your flight search to find flights from Wisconsin to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated March 25, 2026.
Use the filters below to find and compare flights from Wisconsin to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Wed 4/15

7:00 am-8:46 am

Nonstop1h 46m

Chicago Midway

Tue 4/21

2:12 pm-3:55 pm

Nonstop1h 43m

$117

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Tue 6/9

6:05 pm-7:43 pm

Nonstop1h 38m

Chicago O'Hare Intl

Wed 6/10

9:30 am-11:04 am

Nonstop1h 34m

$117

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Tue 4/14

3:15 pm-4:50 pm

Nonstop1h 35m

Chicago Midway

Wed 4/15

4:40 pm-10:30 pm

1 stop5h 50m

$127

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Tue 4/14

8:40 am-4:35 pm

2 stops7h 55m

Chicago Midway

Wed 4/15

6:20 pm-7:50 pm

Nonstop1h 30m

$132

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Thu 4/23

4:42 pm-6:18 pm

Nonstop1h 36m

Chicago O'Hare Intl

Fri 4/24

7:35 pm-9:21 pm

Nonstop1h 46m

$136

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Thu 4/16

5:18 pm-6:54 pm

Nonstop1h 36m

Chicago O'Hare Intl

Sun 4/19

7:20 am-9:06 am

Nonstop1h 46m

$137

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Thu 4/16

5:18 pm-6:54 pm

Nonstop1h 36m

Chicago O'Hare Intl

Sun 4/19

7:20 am-9:06 am

Nonstop1h 46m

$138

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Fri 5/1

11:57 am-12:52 am

1 stop12h 55m

Chicago O'Hare Intl

Wed 5/6

9:42 pm-9:19 am

1 stop11h 37m

$140
Quickest round-trip

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Tue 4/21

7:41 pm-8:50 pm

Nonstop1h 09m

Chicago O'Hare Intl

Tue 4/28

10:30 am-11:32 am

Nonstop1h 02m

$143

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Sat 5/2

8:00 am-9:37 am

Nonstop1h 37m

Chicago O'Hare Intl

Wed 5/6

11:00 pm-12:38 am

Nonstop1h 38m

$147

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Wisconsin to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $434. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Wisconsin to Chicago for around $525.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Wisconsin to Chicago during this time can be as low as $435. In contrast, the most expensive time of day to depart to Chicago is in the evening when prices are around $674.

What is the cheapest Wisconsin to Chicago flight route?

Fly from Milwaukee-Mitchell to Chicago O'Hare Intl for the best Wisconsin - Chicago flight prices

What cabin class options are available on Wisconsin to Chicago flights?

There are 4 cabin classes available to choose from on Wisconsin to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Wisconsin to Chicago flights?

No. A direct flight is the cheapest option for a flight between Wisconsin to Chicago.

Cheap Wisconsin to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Wisconsin to Chicago

Best Price Found

$184

Fastest flight time

0h 50m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Wisconsin in the past 72 hours is $184. The best round-trip flight deal from Wisconsin to Chicago found on momondo in the last 72 hours is $269.
The fastest flight from Wisconsin to Chicago takes 0h 50m
Direct flights go from Wisconsin to Chicago every day.
There are 3 airports in Chicago. From Wisconsin there are direct flights to Chicago O'Hare Intl (ORD).
Search flight deals

  • When did momondo last update prices for flights from Wisconsin to Chicago?

    Prices for flights from Wisconsin to Chicago are refreshed on a daily basis.

  • How many operators does momondo search for flights from Wisconsin to Chicago?

  • How old do you have to be to fly from Wisconsin to Chicago?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Wisconsin to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Wisconsin to Chicago?

Best airlines flying from Wisconsin to Chicago

Compare and see reviews for airlines that fly from Wisconsin to Chicago with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $179Free CancellationRating
7.1
11,493 reviews
Search American Airlines flights
United AirlinesPriceFrom $179Free CancellationRating
7.4
9,478 reviews
Search United Airlines flights

Traveling to a place near Chicago?

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

Why use momondo?

Why should I use momondo to find a flight deal from Wisconsin to Chicago?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Wisconsin to Chicago. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Wisconsin to Chicago with flexible booking policies on momondo?

Yes. All flights to Chicago from Wisconsin on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Wisconsin to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Wisconsin.

I’m not ready to book a flight from Wisconsin to Chicago right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Chicago from Wisconsin. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport