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Midway

$89+ 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 6/28. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MDW
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$179
(Delta)

One-way from

$89
(Cheapflightsfares)

Popular in

November

Cheapest in

March

Average price

$303
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 ($12 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 May 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 May 1, 2025.

This Delta deal was found by Cheapflights users on 4/30. 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 5/297:03 amMSP - MDW
Nonstop1h 33mDelta
Fri 5/309:20 amMDW - MSP
Nonstop1h 39mDelta
Deal found 4/30$179
This Frontier deal was found by Cheapflights users on 4/30. 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.
Sat 6/144:13 pmMSP - MDW
1 stop6h 15mFrontier
Sat 6/216:20 amMDW - MSP
1 stop8h 41mFrontier
Deal found 4/30$184
This Southwest deal was found by Cheapflights users on 4/30. 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 5/296:35 amMSP - MDW
1 stop3h 20mSouthwest
Fri 5/309:15 pmMDW - MSP
Nonstop1h 30mSouthwest
Deal found 4/30$189
This Delta deal was found by Cheapflights users on 4/30. 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 5/3111:51 amATW - MDW
1 stop5h 56mDelta
Sat 6/75:25 pmMDW - ATW
1 stop3h 58mDelta
Deal found 4/30$214
This Delta deal was found by Cheapflights users on 5/1. 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.
Wed 5/145:10 amDLH - MDW
1 stop3h 26mDelta
Sat 5/179:20 amMDW - DLH
1 stop6h 16mDelta
Deal found 5/1$228
This Delta deal was found by Cheapflights users on 4/30. 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.
Fri 6/67:00 amGRB - MDW
1 stop5h 28mDelta
Sun 6/81:09 pmMDW - GRB
1 stop3h 14mDelta
Deal found 4/30$329
This Delta deal was found by Cheapflights users on 5/1. 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 11/207:00 amCWA - MDW
1 stop6h 09mDelta
Sun 11/239:20 amMDW - CWA
1 stop6h 05mDelta
Deal found 5/1$351
This Mytrip deal was found by Cheapflights users on 4/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/238:34 amMSP - MDW
1 stop5h 30mMultiple Airlines
Mon 5/261:15 pmMDW - MSP
2 stops31h 51mMultiple Airlines
Deal found 4/30$368
This Mytrip deal was found by Cheapflights users on 4/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/17:00 amATW - MDW
1 stop24h 45mAllegiant Air
Fri 5/910:59 amMDW - ATW
2 stops35h 17mAllegiant Air
Deal found 4/30$518

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 May 1, 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

Tue 7/1

7:06 am-8:44 am

Nonstop1h 38m

Chicago Midway

Sat 7/5

7:21 pm-9:00 pm

Nonstop1h 39m

$179

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Sat 6/14

4:13 pm-10:28 pm

1 stop6h 15m

Chicago Midway

Sat 6/21

6:20 am-3:01 pm

1 stop8h 41m

$184

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Thu 5/29

6:35 am-9:55 am

1 stop3h 20m

Chicago Midway

Sat 5/31

9:15 pm-10:45 pm

Nonstop1h 30m

$189

AppletonChicago

ATW - MDW

ATWMDW

Appleton Intl

Sat 5/31

11:51 am-5:47 pm

1 stop5h 56m

Chicago Midway

Sat 6/7

5:25 pm-9:23 pm

1 stop3h 58m

$214

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Wed 5/14

5:10 am-8:36 am

1 stop3h 26m

Chicago Midway

Sat 5/17

9:20 am-3:36 pm

1 stop6h 16m

$228

Green BayChicago

GRB - MDW

GRBMDW

Green Bay Austin-Straubel

Fri 6/6

7:00 am-12:28 pm

1 stop5h 28m

Chicago Midway

Sun 6/8

1:09 pm-4:23 pm

1 stop3h 14m

$329

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Fri 5/23

8:34 am-2:04 pm

1 stop5h 30m

Chicago Midway

Mon 5/26

1:15 pm-9:06 pm

2 stops31h 51m

$368

WausauChicago

CWA - MDW

CWAMDW

Wausau Central Wisconsin

Thu 5/29

7:05 am-1:15 pm

1 stop6h 10m

Chicago Midway

Sat 5/31

9:20 am-2:04 pm

1 stop4h 44m

$410

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Sat 6/28

4:13 pm-10:28 pm

1 stop6h 15m

$89

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Sat 5/31

4:15 pm-5:47 pm

Nonstop1h 32m

$90

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/1

Showing 1-10 of 17 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 May 1, 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
4,293 reviews

Overall

8.0

Boarding

8.2

Food

7.1

Entertainment

7.6

Crew

8.6

Comfort

8.0

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
4,293 reviews
Southwest
8.0
Very good
4,293 reviews

Overall

8.0

Boarding

8.2

Food

7.1

Entertainment

7.6

Crew

8.6

Comfort

8.0

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
7,934 reviews
Southwest
8.0
Very good
4,293 reviews

Overall

8.0

Boarding

8.2

Food

7.1

Entertainment

7.6

Crew

8.6

Comfort

8.0

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
4,293 reviews

Overall

8.0

Boarding

8.2

Food

7.1

Entertainment

7.6

Crew

8.6

Comfort

8.0

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
3,287 reviews
Southwest
8.0
Very good
4,293 reviews

Overall

8.0

Boarding

8.2

Food

7.1

Entertainment

7.6

Crew

8.6

Comfort

8.0

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 $89 on Frontier. Other airlines that offer cheap prices include Delta from $90 and Southwest from $100 one-way.

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

    While some choose either Duluth Intl - Chicago Midway or Appleton 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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