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$69+ 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 3/10. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MDW
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$127
(Southwest)

One-way from

$69
(Southwest)
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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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 February 20, 2025.

This Southwest deal was found by Cheapflights users on 2/20. 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 4/34:10 pmMSP - MDW
Nonstop1h 30mSouthwest
Mon 4/74:15 pmMDW - MSP
1 stop6h 00mSouthwest
Deal found 2/20$127
This Frontier deal was found by Cheapflights users on 2/19. 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.
Mon 4/1410:55 amMSP - MDW
1 stop9h 19mFrontier
Wed 4/169:17 pmMDW - MSP
1 stop13h 17mFrontier
Deal found 2/19$130
This Delta deal was found by Cheapflights users on 2/20. 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 3/217:59 amMSP - MDW
Nonstop1h 46mDelta
Mon 3/247:09 pmMDW - MSP
Nonstop1h 37mDelta
Deal found 2/20$132
This Delta deal was found by Cheapflights users on 2/20. 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 3/15:00 amDLH - MDW
1 stop5h 42mDelta
Wed 3/52:08 pmMDW - DLH
2 stops8h 50mDelta
Deal found 2/20$294
This Delta deal was found by Cheapflights users on 2/19. 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 3/76:45 amGRB - MDW
1 stop6h 20mDelta
Tue 3/112:55 pmMDW - GRB
1 stop5h 31mDelta
Deal found 2/19$314
This Delta deal was found by Cheapflights users on 2/19. 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 4/117:00 amATW - MDW
1 stop5h 35mDelta
Sat 4/193:02 pmMDW - ATW
1 stop6h 23mDelta
Deal found 2/19$353
This Delta deal was found by Cheapflights users on 2/20. 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 4/27:00 amCWA - MDW
2 stops5h 36mDelta
Sun 4/610:25 amMDW - CWA
1 stop5h 20mDelta
Deal found 2/20$449

Find flights from Wisconsin to Midway within your budget

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 February 20, 2025.

Fly from

Wisconsin

Fly to

Midway

Route

Depart

Return

Price

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Thu 4/3

4:10 pm-5:40 pm

Nonstop1h 30m

Chicago Midway

Mon 4/7

4:15 pm-10:15 pm

1 stop6h 00m

$127

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Mon 4/14

10:55 am-8:14 pm

1 stop9h 19m

Chicago Midway

Wed 4/16

9:17 pm-10:34 am

1 stop13h 17m

$130

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Fri 3/21

7:59 am-9:45 am

Nonstop1h 46m

Chicago Midway

Fri 3/28

10:25 am-12:00 pm

Nonstop1h 35m

$147

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Fri 8/1

5:10 am-8:36 am

1 stop3h 26m

Chicago Midway

Mon 8/4

1:00 pm-11:37 pm

2 stops10h 37m

$314

Green BayChicago

GRB - MDW

GRBMDW

Green Bay Austin-Straubel

Fri 3/7

6:45 am-1:05 pm

1 stop6h 20m

Chicago Midway

Tue 3/11

2:55 pm-8:26 pm

1 stop5h 31m

$314

AppletonChicago

ATW - MDW

ATWMDW

Appleton Intl

Fri 4/11

7:00 am-12:35 pm

1 stop5h 35m

Chicago Midway

Sat 4/19

3:02 pm-9:25 pm

1 stop6h 23m

$353

WausauChicago

CWA - MDW

CWAMDW

Wausau Central Wisconsin

Wed 4/2

7:00 am-12:36 pm

2 stops5h 36m

Chicago Midway

Sun 4/6

10:25 am-3:45 pm

1 stop5h 20m

$449

AppletonChicago

ATW - MDW

ATWMDW

Appleton Intl

Sat 3/8

3:59 pm-4:36 pm

1 stop24h 37m

Chicago Midway

Mon 3/10

10:54 am-10:47 pm

2 stops35h 53m

$591

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Mon 3/10

5:45 pm-9:45 pm

1 stop4h 00m

$69

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Sun 5/11

6:00 am-7:08 pm

1 stop13h 08m

$72

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 16 results
1
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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.

Travel insights for flights from Wisconsin to Midway

Get recent, data-driven insights about flights from Wisconsin to Midway including ideal travel times, pricing trends, and more.

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 February 20, 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
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Comfort

8.1

Overall

8.1

Crew

8.7

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Comfort

8.1

Overall

8.1

Crew

8.7

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,219 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Comfort

8.1

Overall

8.1

Crew

8.7

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Allegiant Air
7.3
Good
765 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Comfort

8.1

Overall

8.1

Crew

8.7

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Frontier
6.0
Okay
3,355 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Comfort

8.1

Overall

8.1

Crew

8.7

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 $69 on Southwest. Other airlines that offer cheap prices include Frontier from $72 and Delta from $74 one-way.

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

    While some choose either Duluth Intl - Chicago Midway or Wausau Central Wisconsin - 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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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Alternative routes for Wisconsin to Midway

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Top airline flying from Wisconsin to Midway

Discover the top airline that operate flights from Wisconsin to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$178Average$238FlexibilityNo cancel feeOn-time69%
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