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$50+ 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 1/5. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MKE
Jan 15 — Jan 221
Thu 1/15
Thu 1/22
1 adult, Economy
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Cheap 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 December 16, 2025.

This Super.com deal was found by Cheapflights users on 12/14. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/297:38 pmORD - MSP
Nonstop1h 36mFrontier
Mon 1/510:09 pmMSP - ORD
Nonstop1h 45mFrontier
Deal found 12/14$154
This Sun Country Air deal was found by Cheapflights users on 12/13. 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.
Wed 12/3111:45 amORD - MSP
Nonstop1h 39mSun Country Air
Thu 1/13:36 pmMSP - ORD
Nonstop1h 38mSun Country Air
Deal found 12/13$158
This Kiwi.com deal was found by Cheapflights users on 12/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/2612:26 pmORD - MSP
Nonstop1h 36mFrontier
Fri 1/22:57 pmMSP - ORD
Nonstop1h 45mFrontier
Deal found 12/14$162
This Super.com deal was found by Cheapflights users on 12/15. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/2612:26 pmORD - MSP
Nonstop1h 36mFrontier
Mon 12/2910:09 pmMSP - ORD
Nonstop1h 45mFrontier
Deal found 12/15$166
This Sun Country Air deal was found by Cheapflights users on 12/14. 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.
Tue 12/306:44 pmORD - MSP
Nonstop1h 39mSun Country Air
Fri 1/29:00 amMSP - ORD
Nonstop1h 51mSun Country Air
Deal found 12/14$178
This Kiwi.com deal was found by Cheapflights users on 12/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1912:26 pmORD - MSP
Nonstop1h 36mFrontier
Mon 12/2210:09 pmMSP - ORD
Nonstop1h 45mFrontier
Deal found 12/15$181
This Priceline deal was found by Cheapflights users on 12/14. 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.
Mon 12/227:38 pmORD - MSP
Nonstop1h 36mMultiple Airlines
Tue 12/238:36 amMSP - ORD
Nonstop1h 50mMultiple Airlines
Deal found 12/14$193
This American Airlines deal was found by Cheapflights users on 12/14. 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.
Tue 12/308:45 amORD - MKE
Nonstop1h 02mAmerican Airlines
Sun 1/48:08 pmMKE - ORD
Nonstop1h 22mAmerican Airlines
Deal found 12/14$194
This Super.com deal was found by Cheapflights users on 12/15. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/227:38 pmORD - MSP
Nonstop1h 36mFrontier
Fri 12/262:57 pmMSP - ORD
Nonstop1h 45mFrontier
Deal found 12/15$195
This Cheapflightsfares deal was found by Cheapflights users on 12/15. 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.
Sat 12/278:26 pmORD - MSP
Nonstop1h 39mSun Country Air
Thu 1/13:36 pmMSP - ORD
Nonstop1h 38mSun Country Air
Deal found 12/15$197
This American Airlines deal was found by Cheapflights users on 12/14. 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 12/254:39 pmORD - MSN
Nonstop1h 03mAmerican Airlines
Sun 1/49:30 pmMSN - ORD
Nonstop1h 17mAmerican Airlines
Deal found 12/14$203
This American Airlines deal was found by Cheapflights users on 12/15. 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.
Tue 12/306:35 pmORD - MKE
Nonstop1h 03mAmerican Airlines
Sat 1/38:08 pmMKE - ORD
Nonstop1h 22mAmerican Airlines
Deal found 12/15$209

Find flight deals from Chicago to Wisconsin

Keep the following information in mind while searching for Chicago to Wisconsin flight deals. Data was last updated December 16, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$105
(Flightnetwork)

One-way from

$50
(Kiwi.com)

Popular in

February

Cheapest in

November

Average price

$394

Good round-trip deal

$239 or less

Good one-way deal

$138 or less
Provider with most accurate pricing for Chicago (CHI)-Milwaukee-Mitchell flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Milwaukee-Mitchell flights.
Search Deals
From Chicago (CHI) to Wisconsin
Search Deals
One-way flight from Chicago (CHI) to Wisconsin
Search Deals
Highest demand for flights based on searches. 17% potential increase in price ($56 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Wisconsin.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Wisconsin.
Search Deals

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 December 16, 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

MDW - MSP

MDWMSP

Chicago Midway

Wed 2/18

9:50 am-11:32 am

Nonstop1h 42m

Minneapolis St Paul

Wed 2/25

11:22 am-1:07 pm

Nonstop1h 45m

$133

ChicagoMinneapolis

ORD - MSP

ORDMSP

Chicago O'Hare Intl

Thu 1/1

6:14 pm-7:53 pm

Nonstop1h 39m

Minneapolis St Paul

Mon 1/5

4:00 pm-5:38 pm

Nonstop1h 38m

$148

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

Sat 2/21

11:45 am-1:30 pm

Nonstop1h 45m

Minneapolis St Paul

Tue 2/24

4:57 pm-6:37 pm

Nonstop1h 40m

$152

ChicagoMinneapolis

ORD - MSP

ORDMSP

Chicago O'Hare Intl

Thu 1/15

12:58 pm-2:29 pm

Nonstop1h 31m

Minneapolis St Paul

Sat 1/17

6:00 am-7:45 am

Nonstop1h 45m

$157

ChicagoMinneapolis

ORD - MSP

ORDMSP

Chicago O'Hare Intl

Sat 1/17

12:30 pm-2:12 pm

Nonstop1h 42m

Minneapolis St Paul

Wed 1/21

6:55 am-8:40 am

Nonstop1h 45m

$157

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

Sat 1/17

11:45 am-1:32 pm

Nonstop1h 47m

Minneapolis St Paul

Mon 1/19

4:55 pm-6:36 pm

Nonstop1h 41m

$157

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

Sun 1/18

9:50 am-11:34 am

Nonstop1h 44m

Minneapolis St Paul

Thu 1/22

11:22 am-1:09 pm

Nonstop1h 47m

$157

ChicagoMinneapolis

ORD - MSP

ORDMSP

Chicago O'Hare Intl

Wed 12/31

11:45 am-1:24 pm

Nonstop1h 39m

Minneapolis St Paul

Thu 1/1

3:36 pm-5:14 pm

Nonstop1h 38m

$158

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

Thu 1/8

8:40 am-10:20 am

Nonstop1h 40m

Minneapolis St Paul

Sat 1/10

7:05 am-9:00 am

Nonstop1h 55m

$171

ChicagoMinneapolis

ORD - MSP

ORDMSP

Chicago O'Hare Intl

Mon 1/12

2:17 pm-3:48 pm

Nonstop1h 31m

Minneapolis St Paul

Wed 1/14

6:00 am-7:45 am

Nonstop1h 45m

$171

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/15

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, September is the cheapest month in which you can book a flight from Chicago to Wisconsin (average of $178). Flying from Chicago to Wisconsin in February is currently the most expensive (average of $267). 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 December 16, 2025.

One of the essential ways to save on airfare from Chicago to Wisconsin is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the afternoon could potentially save you up to 17% on airfare.

What is the cheapest day to fly from Chicago to Wisconsin?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Wisconsin. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago to Wisconsin flight should consider departing on Thursday at noon when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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 December 16, 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
9,094 reviews

Comfort

7.3

Entertainment

7.1

Overall

7.4

Boarding

7.7

Crew

8.1

Food

6.6

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.
United Airlines
7.4
Good
9,094 reviews
United Airlines
7.4
Good
9,094 reviews

Comfort

7.3

Entertainment

7.1

Overall

7.4

Boarding

7.7

Crew

8.1

Food

6.6

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.
American Airlines
7.2
Good
11,048 reviews
United Airlines
7.4
Good
9,094 reviews

Comfort

7.3

Entertainment

7.1

Overall

7.4

Boarding

7.7

Crew

8.1

Food

6.6

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.

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 $157, Delta can have you in Wisconsin from Chicago in 1h 31m. There are 333 mi between Chicago and Wisconsin. Generally, flights for this route are nonstop.

  • 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 (81%), United Airlines (75%), Air Canada( 72%).

  • 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, September is the cheapest month in which you can book a flight from Chicago to Wisconsin (average of $178). Flying from Chicago to Wisconsin in February is currently the most expensive (average of $267). 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 December 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$179Average$280FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$180Average$315FlexibilityNo cancel feeOn-time69%

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