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Cheap flights from Wisconsin to Chicago from $49

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 9/13. 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

Southwest Logo
2:10 pm - 3:40 pmMSP-MDW
1h 30mnonstop
Southwest Logo
7:35 pm - 9:00 pmMDW-MSP
1h 25mnonstop
$97Southwest
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Thu, Oct 23 - Sat, Oct 25
Southwest Logo
10:25 am - 11:50 amMSP-MDW
1h 25mnonstop
Southwest Logo
7:25 am - 2:30 pmMDW-MSP
7h 05m1 stop
$107Southwest
Find Deal
Sat, Sep 6 - Tue, Sep 9
Southwest Logo
9:55 am - 11:20 amMSP-MDW
1h 25mnonstop
Southwest Logo
2:35 pm - 4:05 pmMDW-MSP
1h 30mnonstop
$110Southwest
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Fri, Sep 5 - Mon, Sep 8
Southwest Logo
2:45 pm - 4:15 pmMSP-MDW
1h 30mnonstop
Southwest Logo
2:05 pm - 10:25 pmMDW-MSP
8h 20m2 stops
$112Southwest
Find Deal
Sat, Sep 6 - Tue, Sep 9
Southwest Logo
4:30 pm - 9:55 pmMSP-MDW
5h 25m1 stop
Southwest Logo
5:40 pm - 10:25 pmMDW-MSP
4h 45m1 stop
$117Southwest
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Wed, Sep 17 - Tue, Sep 30
Delta Logo
4:05 pm - 5:37 pmMSP-MDW
1h 32mnonstop
Delta Logo
1:43 pm - 3:25 pmMDW-MSP
1h 42mnonstop
$155Delta
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Fri, Aug 22 - Sat, Aug 23
Delta Logo
7:13 am - 8:50 amMSP-MDW
1h 37mnonstop
Delta Logo
1:43 pm - 3:25 pmMDW-MSP
1h 42mnonstop
$157Delta
Find Deal
Wed, Aug 27 - Wed, Sep 3
Delta Logo
4:05 pm - 5:37 pmMSP-MDW
1h 32mnonstop
Delta Logo
9:15 am - 10:53 amMDW-MSP
1h 38mnonstop
$178Delta
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Fri, Aug 22 - Mon, Aug 25
Frontier Logo
12:31 pm - 11:17 pmMSP-MDW
10h 46m1 stop
Frontier Logo
6:20 am - 2:51 pmMDW-MSP
8h 31m1 stop
$188Frontier
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Thu, Aug 14 - Sat, Aug 16
Frontier Logo
12:55 pm - 8:54 pmMSP-MDW
7h 59m1 stop
Frontier Logo
6:20 am - 2:51 pmMDW-MSP
8h 31m1 stop
$194Frontier
Find Deal
Thu, Aug 14 - Sat, Aug 16

Frontier flights from Wisconsin to Chicago Midway Airport

Our best Frontier deals on Wisconsin to Chicago Midway Airport flight tickets
Frontier
Aug 2
MSP4:14 pmMinneapolis St Paul
6h 21m
1 stop
MDW10:35 pmChicago Midway
Aug 9
MDW6:20 amChicago Midway
8h 31m
1 stop
MSP2:51 pmMinneapolis St Paul
$178
Find similar
Frontier
Aug 14
MSP12:31 pmMinneapolis St Paul
10h 46m
1 stop
MDW11:17 pmChicago Midway
Aug 16
MDW6:20 amChicago Midway
8h 31m
1 stop
MSP2:51 pmMinneapolis St Paul
$188
Find similar
Frontier
Aug 14
MSP12:55 pmMinneapolis St Paul
7h 59m
1 stop
MDW8:54 pmChicago Midway
Aug 16
MDW6:20 amChicago Midway
8h 31m
1 stop
MSP2:51 pmMinneapolis St Paul
$194
Find similar

Delta flights from Wisconsin to Chicago Midway Airport

Our best Delta deals on Wisconsin to Chicago Midway Airport flight tickets
Delta
Aug 22
MSP4:05 pmMinneapolis St Paul
1h 32m
MDW5:37 pmChicago Midway
Aug 23
MDW1:43 pmChicago Midway
1h 42m
MSP3:25 pmMinneapolis St Paul
$155
Find similar
Delta
Aug 27
MSP7:13 amMinneapolis St Paul
1h 37m
MDW8:50 amChicago Midway
Sep 3
MDW1:43 pmChicago Midway
1h 42m
MSP3:25 pmMinneapolis St Paul
$157
Find similar
Delta
Aug 22
MSP4:05 pmMinneapolis St Paul
1h 32m
MDW5:37 pmChicago Midway
Aug 25
MDW9:15 amChicago Midway
1h 38m
MSP10:53 amMinneapolis St Paul
$178
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Wisconsin to Chicago Midway Airport 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 August 2, 2025.
Use the filters below to find and compare flights from Wisconsin to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Thu 10/23

2:10 pm-3:40 pm

Nonstop1h 30m

Chicago Midway

Sat 10/25

7:35 pm-9:00 pm

Nonstop1h 25m

$97

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Sat 9/6

10:25 am-11:50 am

Nonstop1h 25m

Chicago Midway

Tue 9/9

7:25 am-2:30 pm

1 stop7h 05m

$107

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Fri 9/5

9:55 am-11:20 am

Nonstop1h 25m

Chicago Midway

Mon 9/8

2:35 pm-4:05 pm

Nonstop1h 30m

$110

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Sat 9/6

2:45 pm-4:15 pm

Nonstop1h 30m

Chicago Midway

Tue 9/9

2:05 pm-10:25 pm

2 stops8h 20m

$112

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Wed 9/17

4:30 pm-9:55 pm

1 stop5h 25m

Chicago Midway

Tue 9/30

5:40 pm-10:25 pm

1 stop4h 45m

$117

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Fri 8/22

4:05 pm-5:37 pm

Nonstop1h 32m

Chicago Midway

Sat 8/23

1:43 pm-3:25 pm

Nonstop1h 42m

$155

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Wed 8/27

7:13 am-8:50 am

Nonstop1h 37m

Chicago Midway

Wed 9/3

1:43 pm-3:25 pm

Nonstop1h 42m

$157

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Fri 8/22

4:05 pm-5:37 pm

Nonstop1h 32m

Chicago Midway

Mon 8/25

9:15 am-10:53 am

Nonstop1h 38m

$178

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Thu 8/14

12:31 pm-11:17 pm

1 stop10h 46m

Chicago Midway

Sat 8/16

6:20 am-2:51 pm

1 stop8h 31m

$188

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Thu 8/14

12:55 pm-8:54 pm

1 stop7h 59m

Chicago Midway

Sat 8/16

6:20 am-2:51 pm

1 stop8h 31m

$194

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 Midway Airport

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 airline that flies from Wisconsin to Chicago Midway?

Delta, Southwest, and Frontier are the most popular carriers operating from Wisconsin to Chicago Midway

Cheap Wisconsin to Chicago Midway Airport flight deals and tips

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

Best Price Found

$49

Fastest flight time

1h 25m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Wisconsin in the past 72 hours is $49. The best round-trip flight deal from Wisconsin to Chicago Midway Airport found on momondo in the last 72 hours is $97.
The fastest flight from Wisconsin to Chicago Midway Airport takes 1h 25m
Direct flights go from Wisconsin to Chicago Midway Airport every day.
Search flight deals

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

    Prices for flights from Wisconsin to Chicago Midway Airport refresh daily.

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

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

    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 Midway Airport.

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

    The necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Traveling to a place near Chicago?

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

Why use momondo?

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

Finding the right flight to Chicago from Wisconsin is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

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?

momondo helps you find the best flight between Wisconsin and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

Yes. momondo can track prices for Wisconsin to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

An easier way to manage your Chicago Midway Airport trip

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