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$49+ Cheap flights from Wisconsin to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/19. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MDW
Apr 30 — May 71
Wed 4/30
Wed 5/7
1 adult, Economy
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Cheap flight deals from Wisconsin to Midway

Keep the following information in mind while searching for Wisconsin to Midway flight deals. Data was last updated April 25, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$92
(Southwest)

One-way from

$49
(Southwest)

Popular in

November

Cheapest in

March

Average price

$357
Provider with most accurate pricing for Milwaukee-Mitchell-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Milwaukee-Mitchell-Chicago (CHI) flights.
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From Wisconsin to Chicago Midway
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One-way flight from Wisconsin to Chicago Midway
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Highest demand for flights based on searches. 3% potential increase in price ($10 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Find flight deals from Wisconsin to Midway

Cheapest flights from Wisconsin to Midway
Explore the most affordable flight options available from Wisconsin to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 25, 2025.

This Southwest deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2912:25 pmMSP - MDW
Nonstop1h 30mSouthwest
Mon 6/25:20 amMDW - MSP
2 stops6h 20mSouthwest
Deal found 4/24$92
This Delta deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/711:40 amMSP - MDW
Nonstop1h 35mDelta
Tue 6/171:47 pmMDW - MSP
Nonstop1h 38mDelta
Deal found 4/24$114
This Frontier deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/293:13 pmMSP - MDW
1 stop6h 43mFrontier
Sun 6/16:20 amMDW - MSP
1 stop8h 12mFrontier
Deal found 4/24$198
This Delta deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1011:11 amATW - MDW
1 stop5h 10mDelta
Wed 5/149:20 amMDW - ATW
1 stop6h 20mDelta
Deal found 4/25$209
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/207:55 amDLH - MDW
1 stop5h 20mDelta
Tue 5/277:25 pmMDW - DLH
1 stop4h 13mDelta
Deal found 4/23$258
This Delta deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/1912:10 pmGRB - MDW
1 stop5h 30mDelta
Sun 6/229:21 amMDW - GRB
1 stop6h 23mDelta
Deal found 4/25$549

Cheapflights Fare Finder

Customize your flight search to find flights from Wisconsin to Midway 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, Cheapflights users made 2,558,603 searches. Data last updated April 25, 2025.
Use the filters below to find and compare flights from Wisconsin to Chicago Midway Airport that are best for you.

Fly from

Wisconsin

Fly to

Midway

Route

Depart

Return

Price

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Thu 5/29

12:25 pm-1:55 pm

Nonstop1h 30m

Chicago Midway

Mon 6/2

5:20 am-11:40 am

2 stops6h 20m

$92

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Sat 6/7

11:40 am-1:15 pm

Nonstop1h 35m

Chicago Midway

Tue 6/17

1:47 pm-3:25 pm

Nonstop1h 38m

$114

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Thu 5/29

3:13 pm-9:56 pm

1 stop6h 43m

Chicago Midway

Sun 6/1

6:20 am-2:32 pm

1 stop8h 12m

$198

AppletonChicago

ATW - MDW

ATWMDW

Appleton Intl

Sat 5/10

11:11 am-4:21 pm

1 stop5h 10m

Chicago Midway

Wed 5/14

9:20 am-3:40 pm

1 stop6h 20m

$209

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Tue 5/20

7:55 am-1:15 pm

1 stop5h 20m

Chicago Midway

Tue 5/27

7:25 pm-11:38 pm

1 stop4h 13m

$258

Green BayChicago

GRB - MDW

GRBMDW

Green Bay Austin-Straubel

Thu 6/19

12:10 pm-5:40 pm

1 stop5h 30m

Chicago Midway

Sun 6/22

9:21 am-3:44 pm

1 stop6h 23m

$549

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Mon 5/19

4:40 pm-10:00 pm

1 stop5h 20m

$49

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Sat 9/13

4:30 pm-6:07 pm

Nonstop1h 37m

$76

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Sat 5/24

3:13 pm-10:02 pm

1 stop6h 49m

$89

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Sun 6/15

7:35 pm-7:46 pm

1 stop24h 11m

$103

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/24

Showing 1-10 of 14 results
1
2

Best time to book a flight from Wisconsin to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Wisconsin with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Wisconsin to Chicago Midway Airport

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated April 25, 2025.
To help decide which airline to fly from Wisconsin to Chicago, see what other customers have to say about Southwest, Delta and Allegiant Air. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,287 reviews

Crew

8.6

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Overall

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Crew

8.6

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Overall

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,920 reviews
Southwest
8.0
Very good
4,287 reviews

Crew

8.6

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Overall

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Allegiant Air
7.3
Good
734 reviews
Southwest
8.0
Very good
4,287 reviews

Crew

8.6

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Overall

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Frontier
6.0
Okay
3,283 reviews
Southwest
8.0
Very good
4,287 reviews

Crew

8.6

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Overall

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

Related info for your journey

Find useful and relevant information for your journey from Wisconsin to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines to fly from Wisconsin to Chicago Midway Airport one-way?

    One-way options have recently been found by users for as low as $49 on Southwest. Other airlines that offer cheap prices include Delta from $76 and Frontier from $89 one-way.

  • What are the most popular routes from Wisconsin to Chicago Midway Airport?

    While some choose either Appleton Intl - Chicago Midway or Duluth Intl - Chicago Midway, Minneapolis St Paul - Chicago Midway is the most popular route from Wisconsin to Chicago Midway Airport.

  • Can I find deals for flights from Wisconsin to Midway that include hotel bookings?

    Yes. In addition to deals on Wisconsin to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Wisconsin to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Wisconsin to Midway.

  • Can I find deals for business class flights from Wisconsin to Midway?

    Yes. Cheapflights offers flight deals from Wisconsin to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Wisconsin to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Wisconsin to Chicago Midway Airport (average of $160). Flying from Wisconsin to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Wisconsin?

Book flights to Wisconsin if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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Alternative routes for Wisconsin to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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