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$49+ 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 1/30. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MKE
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
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 September 11, 2025.

Round-trip from

$92
(Sun Country Air)

One-way from

$49
(Priceline)

Popular in

December

Cheapest in

September

Average price

$183

Good round-trip deal

$199 or less

Good one-way deal

$88 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. 25% potential increase in price ($95 potential increase over avg. RT price).
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Cheapest flight prices on average. 10% potential price decrease ($28 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 11, 2025.

This Sun Country Air deal was found by Cheapflights users on 9/11. 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 11/76:14 pmORD - MSP
Nonstop1h 42mSun Country Air
Sun 11/98:54 amMSP - ORD
Nonstop1h 45mSun Country Air
Deal found 9/11$92
This Gotogate deal was found by Cheapflights users on 9/10. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/247:15 pmORD - MSP
Nonstop1h 43mSun Country Air
Mon 10/279:00 amMSP - ORD
Nonstop1h 39mSun Country Air
Deal found 9/10$93
This United Airlines deal was found by Cheapflights users on 9/11. 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.
Tue 9/308:51 amORD - MSP
Nonstop1h 32mUnited Airlines
Wed 10/16:00 amMSP - ORD
Nonstop1h 43mUnited Airlines
Deal found 9/11$101
This Southwest deal was found by Cheapflights users on 9/11. 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.
Wed 10/227:45 amMDW - MSP
Nonstop1h 25mSouthwest
Sat 10/2510:25 amMSP - MDW
Nonstop1h 30mSouthwest
Deal found 9/11$101
This Cheapflightsfares deal was found by Cheapflights users on 9/10. 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 Cheapflightsfares 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 9/10$104
This Sun Country Air deal was found by Cheapflights users on 9/10. 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 12/197:38 pmORD - MSP
Nonstop1h 39mSun Country Air
Mon 12/295:00 pmMSP - ORD
Nonstop1h 38mSun Country Air
Deal found 9/10$105
This Cheapflightsfares deal was found by Cheapflights users on 9/11. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/2410:21 amORD - MSP
Nonstop1h 39mSun Country Air
Fri 12/265:06 pmMSP - ORD
Nonstop1h 38mSun Country Air
Deal found 9/11$114
This American Airlines deal was found by Cheapflights users on 9/10. 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.
Mon 10/67:36 amORD - MSP
Nonstop1h 39mAmerican Airlines
Tue 10/75:00 amMSP - ORD
Nonstop1h 32mAmerican Airlines
Deal found 9/10$115
This Delta deal was found by Cheapflights users on 9/11. 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 12/161:50 pmMDW - MSP
Nonstop1h 40mDelta
Mon 12/223:30 pmMSP - MDW
Nonstop1h 49mDelta
Deal found 9/11$115
This United Airlines deal was found by Cheapflights users on 9/10. 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.
Fri 10/39:40 pmORD - MSP
Nonstop1h 35mUnited Airlines
Tue 10/76:00 amMSP - ORD
Nonstop1h 43mUnited Airlines
Deal found 9/10$117
This Delta deal was found by Cheapflights users on 9/11. 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 10/41:43 pmMDW - MSP
Nonstop1h 46mDelta
Sun 10/57:14 amMSP - MDW
Nonstop1h 39mDelta
Deal found 9/11$117
This Sun Country Air deal was found by Cheapflights users on 9/10. 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 12/197:38 pmORD - MSP
Nonstop1h 39mSun Country Air
Tue 12/303:48 pmMSP - ORD
Nonstop1h 38mSun Country Air
Deal found 9/10$118

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 September 11, 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

Tue 10/14

12:45 pm-2:21 pm

Nonstop1h 36m

Minneapolis St Paul

Tue 10/14

6:30 pm-8:18 pm

Nonstop1h 48m

$101

ChicagoMinneapolis

ORD - MSP

ORDMSP

Chicago O'Hare Intl

Sat 10/18

6:08 am-7:35 am

Nonstop1h 27m

Minneapolis St Paul

Thu 10/23

6:59 am-8:30 am

Nonstop1h 31m

$115

ChicagoMinneapolis

ORD - MSP

ORDMSP

Chicago O'Hare Intl

Fri 10/3

9:40 pm-11:15 pm

Nonstop1h 35m

Minneapolis St Paul

Sat 10/4

3:17 pm-4:58 pm

Nonstop1h 41m

$117

ChicagoMinneapolis

ORD - MSP

ORDMSP

Chicago O'Hare Intl

Sat 10/11

8:57 am-10:30 am

Nonstop1h 33m

Minneapolis St Paul

Sun 10/12

7:50 pm-9:19 pm

Nonstop1h 29m

$117

ChicagoMinneapolis

ORD - MSP

ORDMSP

Chicago O'Hare Intl

Sat 11/1

2:20 pm-3:50 pm

Nonstop1h 30m

Minneapolis St Paul

Mon 11/3

6:29 pm-8:10 pm

Nonstop1h 41m

$117

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

Wed 10/29

9:20 am-11:02 am

Nonstop1h 42m

Minneapolis St Paul

Sun 11/2

7:15 am-8:55 am

Nonstop1h 40m

$117

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

Sat 10/4

1:43 pm-3:29 pm

Nonstop1h 46m

Minneapolis St Paul

Sun 10/5

7:14 am-8:53 am

Nonstop1h 39m

$117

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

Thu 10/23

7:45 am-9:10 am

Nonstop1h 25m

Minneapolis St Paul

Mon 10/27

5:15 am-6:45 am

Nonstop1h 30m

$132

ChicagoMinneapolis

ORD - MSP

ORDMSP

Chicago O'Hare Intl

Fri 10/24

10:10 pm-11:40 pm

Nonstop1h 30m

Minneapolis St Paul

Sun 10/26

7:00 am-8:42 am

Nonstop1h 42m

$133

ChicagoMinneapolis

ORD - MSP

ORDMSP

Chicago O'Hare Intl

Fri 10/10

9:40 pm-11:15 pm

Nonstop1h 35m

Minneapolis St Paul

Sun 10/12

6:00 am-7:43 am

Nonstop1h 43m

$133

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 60 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 September 11, 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 September 11, 2025.

The most flights from CHI to USWI are scheduled on a Thursday (52 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (37 on average).

How much does it cost to fly round-trip from Chicago to Wisconsin?

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 September 11, 2025.
See what other customers who have flown with United Airlines and American Airlines 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.
United Airlines
7.4
Good
8,937 reviews

Comfort

7.3

Overall

7.4

Boarding

7.7

Food

6.6

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
United Airlines
7.4
Good
8,937 reviews
United Airlines
7.4
Good
8,937 reviews

Comfort

7.3

Overall

7.4

Boarding

7.7

Food

6.6

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,937 reviews

Comfort

7.3

Overall

7.4

Boarding

7.7

Food

6.6

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

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.

  • How long is the flight from Chicago to Wisconsin?

    For as low as $132, United Airlines can have you in Wisconsin from Chicago in 1h 25m. There are 348 mi between Chicago and Wisconsin. Generally, flights for this route are nonstop.

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

    $51 is the cheapest one-way deal found within the past few days, from United Airlines. You may also be able to find cheap deals on Delta and Southwest, with prices starting from $51 and $51, 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 - Madison Truax Field 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: Qatar Airways (77%), Republic Airways (75%), Copa Airlines( 69%).

  • What are the cheapest flights from Chicago to Wisconsin?

    On average you can expect to pay $279 for a flight from Chicago to Wisconsin. The cheapest flight overall is $224 while the most popular route, (Chicago O'Hare Intl - Minneapolis St Paul) is currently priced at $65.

  • 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$179Average$297FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$180Average$303FlexibilityNo cancel feeOn-time69%

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