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$58+ Cheap flights from Chicago (CHI) to Wisconsin

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 8/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MKE
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
1 adult, Economy
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Cheap flight deals from Chicago to Wisconsin

Keep the following information in mind while searching for Chicago to Wisconsin flight deals. Data was last updated July 31, 2025.

Round-trip from

$92
(Sun Country Air)

One-way from

$58
(Cheapflightsfares)

Popular in

December

Cheapest in

April

Average price

$239

Good round-trip deal

$224 or less

Good one-way deal

$98 or less
From Chicago (CHI) to Wisconsin
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One-way flight from Chicago (CHI) to Wisconsin
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Highest demand for flights based on searches. 26% potential increase in price ($102 potential increase over avg. RT price).
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Cheapest flight prices on average. 11% potential price decrease ($28 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Wisconsin.
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Price to beat on a one-way flight from Chicago (CHI) to Wisconsin.
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Find flight deals from Chicago to Wisconsin

Cheapest flights from Chicago to Wisconsin
Explore the most affordable flight options available from Chicago to Wisconsin. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 31, 2025.

This Sun Country Air deal was found by Cheapflights users on 7/30. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/147:26 pmORD - MSP
Nonstop1h 42mSun Country Air
Mon 11/179:00 amMSP - ORD
Nonstop1h 45mSun Country Air
Deal found 7/30$92
This Delta deal was found by Cheapflights users on 7/30. 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 9/138:52 amORD - MSP
Nonstop1h 38mDelta
Sat 9/203:29 pmMSP - ORD
Nonstop1h 32mDelta
Deal found 7/30$97
This Delta deal was found by Cheapflights users on 7/30. 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 9/137:15 pmMDW - MSP
Nonstop1h 44mDelta
Sat 9/207:14 amMSP - MDW
Nonstop1h 39mDelta
Deal found 7/30$97
This Southwest deal was found by Cheapflights users on 7/29. 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.
Tue 8/2610:10 amMDW - MSP
Nonstop1h 40mSouthwest
Wed 8/276:00 amMSP - MDW
1 stop3h 50mSouthwest
Deal found 7/29$107
This American Airlines deal was found by Cheapflights users on 7/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/133:31 pmORD - MSP
Nonstop1h 31mAmerican Airlines
Mon 9/155:35 amMSP - ORD
Nonstop1h 40mAmerican Airlines
Deal found 7/30$110
This United Airlines deal was found by Cheapflights users on 7/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/307:19 amORD - MSP
Nonstop1h 35mUnited Airlines
Mon 9/16:00 amMSP - ORD
Nonstop1h 43mUnited Airlines
Deal found 7/30$119
This FlightHub deal was found by Cheapflights users on 7/30. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/2510:10 amORD - MSP
Nonstop1h 47mMultiple Airlines
Wed 8/279:22 amMSP - ORD
1 stop7h 04mMultiple Airlines
Deal found 7/30$132
This United Airlines deal was found by Cheapflights users on 7/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/272:03 pmORD - MKE
Nonstop1h 06mUnited Airlines
Wed 9/38:30 amMKE - ORD
Nonstop1h 10mUnited Airlines
Deal found 7/29$179
This American Airlines deal was found by Cheapflights users on 7/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/139:25 amORD - GRB
Nonstop1h 16mAmerican Airlines
Wed 9/174:35 pmGRB - ORD
Nonstop1h 21mAmerican Airlines
Deal found 7/30$179
This American Airlines deal was found by Cheapflights users on 7/31. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/298:12 amORD - ATW
Nonstop1h 05mAmerican Airlines
Sun 8/319:47 amATW - ORD
Nonstop1h 15mAmerican Airlines
Deal found 7/31$179
This Priceline deal was found by Cheapflights users on 7/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/26:20 amMDW - MSP
1 stop8h 31mFrontier
Sat 8/24:14 pmMSP - MDW
1 stop6h 21mFrontier
Deal found 7/29$179
This American Airlines deal was found by Cheapflights users on 7/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/218:17 amORD - MSN
Nonstop1h 01mAmerican Airlines
Sun 8/248:14 pmMSN - ORD
Nonstop1h 05mAmerican Airlines
Deal found 7/30$179

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Wisconsin 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 July 31, 2025.
Use the filters below to find and compare flights from Chicago to Wisconsin that are best for you.

Fly from

Chicago

Fly to

Wisconsin

Route

Depart

Return

Price

ChicagoMinneapolis

ORD - MSP

ORDMSP

Chicago O'Hare Intl

Fri 11/14

7:26 pm-9:08 pm

Nonstop1h 42m

Minneapolis St Paul

Mon 11/17

9:00 am-10:45 am

Nonstop1h 45m

$92

ChicagoMinneapolis

ORD - MSP

ORDMSP

Chicago O'Hare Intl

Sat 9/13

8:52 am-10:30 am

Nonstop1h 38m

Minneapolis St Paul

Sat 9/20

3:29 pm-5:01 pm

Nonstop1h 32m

$97

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

Sat 9/13

7:15 pm-8:59 pm

Nonstop1h 44m

Minneapolis St Paul

Sat 9/20

7:14 am-8:53 am

Nonstop1h 39m

$97

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

Tue 8/26

10:10 am-11:50 am

Nonstop1h 40m

Minneapolis St Paul

Wed 8/27

6:00 am-9:50 am

1 stop3h 50m

$107

ChicagoMinneapolis

ORD - MSP

ORDMSP

Chicago O'Hare Intl

Sat 9/13

3:31 pm-5:02 pm

Nonstop1h 31m

Minneapolis St Paul

Mon 9/15

5:35 am-7:15 am

Nonstop1h 40m

$110

ChicagoMinneapolis

ORD - MSP

ORDMSP

Chicago O'Hare Intl

Sat 8/30

7:19 am-8:54 am

Nonstop1h 35m

Minneapolis St Paul

Mon 9/1

6:00 am-7:43 am

Nonstop1h 43m

$119

ChicagoMinneapolis

ORD - MSP

ORDMSP

Chicago O'Hare Intl

Mon 8/25

10:10 am-11:57 am

Nonstop1h 47m

Minneapolis St Paul

Wed 8/27

9:22 am-4:26 pm

1 stop7h 04m

$132

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

Sat 8/16

6:20 am-2:51 pm

1 stop8h 31m

Minneapolis St Paul

Sat 8/16

4:08 pm-10:33 pm

1 stop6h 25m

$179

ChicagoGreen Bay

ORD - GRB

ORDGRB

Chicago O'Hare Intl

Sat 9/13

9:25 am-10:41 am

Nonstop1h 16m

Green Bay Austin-Straubel

Wed 9/17

4:35 pm-5:56 pm

Nonstop1h 21m

$179

ChicagoMilwaukee

ORD - MKE

ORDMKE

Chicago O'Hare Intl

Wed 8/27

2:03 pm-3:09 pm

Nonstop1h 06m

Milwaukee-Mitchell

Wed 9/3

8:30 am-9:40 am

Nonstop1h 10m

$179

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Showing 1-10 of 57 results
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Best time to book a flight from Chicago to Wisconsin

Have a flexible travel schedule? Discover the best time to fly to Wisconsin from Chicago 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 Chicago to Wisconsin

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

Currently, February is the cheapest month in which you can book a flight from Chicago to Wisconsin (average of $280). Flying from Chicago to Wisconsin in June is currently the most expensive (average of $376). 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.

What is the cheapest time of day to fly from CHI to WI?

Find hourly flight availability from Chicago to Wisconsin. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 31, 2025.

When flying from Chicago to Wisconsin, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Chicago to Wisconsin

Explore weekly flight availability from Chicago to Wisconsin. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated July 31, 2025.

The most flights from CHI to USWI are scheduled on a Thursday (49 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (35 on average).

Reviews of airlines servicing Wisconsin

Get insights into the airlines that provide service to Wisconsin. 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 Wisconsin. Reviews last updated July 31, 2025.
See what other customers who have flown with Alaska Airlines, Southwest, and Delta from Chicago to Wisconsin have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Entertainment

7.1

Crew

8.5

Boarding

8.1

Overall

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Entertainment

7.1

Crew

8.5

Boarding

8.1

Overall

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Southwest
8.0
Very good
4,244 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Entertainment

7.1

Crew

8.5

Boarding

8.1

Overall

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Delta
8.0
Very good
7,980 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Entertainment

7.1

Crew

8.5

Boarding

8.1

Overall

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
United Airlines
7.4
Good
8,902 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Entertainment

7.1

Crew

8.5

Boarding

8.1

Overall

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Entertainment

7.1

Crew

8.5

Boarding

8.1

Overall

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Wisconsin. 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 Chicago to Wisconsin one-way?

    $58 is the cheapest one-way deal found within the past few days, from Sun Country Air. You may also be able to find cheap deals on Southwest and Delta, with prices starting from $59 and $62, respectively.

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

    Most travelers choose Chicago O'Hare Intl - Minneapolis St Paul, Chicago Midway - Minneapolis St Paul or Chicago O'Hare Intl - Duluth Intl when deciding on the best route from Chicago to Wisconsin.

  • What are the most reliable airlines from Chicago to Wisconsin?

    Before booking your flight to Wisconsin from Chicago, check out the most reliable airlines to get you to your destination on time: Republic Airways (100%), Air Canada (76%), United Airlines( 74%).

  • What are the cheapest flights from Chicago to Wisconsin?

    On average you can expect to pay $367 for a flight from Chicago to Wisconsin. The cheapest flight overall is $279 while the most popular route, (Chicago O'Hare Intl - Minneapolis St Paul) is currently priced at $90.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Chicago to Wisconsin 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 Chicago to Wisconsin?

    Currently, February is the cheapest month in which you can book a flight from Chicago to Wisconsin (average of $280). Flying from Chicago to Wisconsin in June is currently the most expensive (average of $376). 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

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Alternative routes for Chicago to Wisconsin

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Chicago to Wisconsin

Discover the top 2 airlines that operate flights from Chicago to Wisconsin. 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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$179Average$308FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$179Average$302FlexibilityNo cancel feeOn-time71%

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