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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 4/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MKE
Apr 5 — Apr 121
Sat 4/5
Sat 4/12
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 March 31, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$106
(eDestinos)

One-way from

$58
(Cheapflightsfares)

Popular in

December

Cheapest in

September

Good round-trip deal

$180 or less

Good one-way deal

$98 or less
Provider with most accurate pricing for Chicago (CHI)-Milwaukee-Mitchell flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Milwaukee-Mitchell flights.
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From Chicago (CHI) to Wisconsin
Search Deals
One-way flight from Chicago (CHI) to Wisconsin
Search Deals
Highest demand for flights based on searches. 20% potential increase in price ($76 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 9% potential price decrease ($26 potential savings vs. average RT price).
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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 March 31, 2025.

This eDestinos deal was found by Cheapflights users on 3/30. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/28:05 pmORD - MSP
Nonstop1h 44mSun Country Air
Sun 5/45:30 pmMSP - ORD
Nonstop1h 39mSun Country Air
Deal found 3/30$106
This Trip.com deal was found by Cheapflights users on 3/31. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/255:23 pmORD - MSP
1 stop7h 12mMultiple Airlines
Sun 4/274:14 pmMSP - ORD
Nonstop1h 39mMultiple Airlines
Deal found 3/31$145
This CheapOair deal was found by Cheapflights users on 3/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/255:23 pmORD - MSP
1 stop7h 12mFrontier
Mon 4/286:00 amMSP - ORD
1 stop17h 38mFrontier
Deal found 3/30$160
This CheapOair deal was found by Cheapflights users on 3/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/258:01 pmMDW - MSP
1 stop28h 34mFrontier
Mon 4/286:00 amMSP - MDW
1 stop13h 06mFrontier
Deal found 3/30$160
This American Airlines deal was found by Cheapflights users on 3/30. 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.
Wed 5/148:35 amORD - MKE
Nonstop0h 47mAmerican Airlines
Wed 5/216:23 pmMKE - ORD
Nonstop1h 00mAmerican Airlines
Deal found 3/30$175
This American Airlines deal was found by Cheapflights users on 3/30. 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 5/101:15 pmORD - MSP
Nonstop1h 33mAmerican Airlines
Sat 5/106:10 pmMSP - ORD
Nonstop1h 35mAmerican Airlines
Deal found 3/30$178
This American Airlines deal was found by Cheapflights users on 3/31. 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.
Mon 4/218:25 pmORD - ATW
Nonstop1h 18mAmerican Airlines
Sat 4/266:20 pmATW - ORD
Nonstop1h 13mAmerican Airlines
Deal found 3/31$179
This Delta deal was found by Cheapflights users on 3/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/1910:20 amORD - MSP
Nonstop1h 39mDelta
Sun 4/201:55 pmMSP - ORD
Nonstop1h 34mDelta
Deal found 3/31$179
This American Airlines deal was found by Cheapflights users on 3/30. 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 4/2410:15 pmORD - MSN
Nonstop1h 05mAmerican Airlines
Mon 4/284:30 pmMSN - ORD
Nonstop1h 12mAmerican Airlines
Deal found 3/30$179
This American Airlines deal was found by Cheapflights users on 3/30. 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 4/245:11 pmORD - GRB
Nonstop0h 59mAmerican Airlines
Mon 4/286:40 pmGRB - ORD
Nonstop1h 10mAmerican Airlines
Deal found 3/30$181
This Southwest deal was found by Cheapflights users on 3/30. 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.
Sat 4/198:00 amMDW - MSP
Nonstop1h 25mSouthwest
Wed 4/234:00 pmMSP - MDW
Nonstop1h 30mSouthwest
Deal found 3/30$181
This Delta deal was found by Cheapflights users on 3/30. 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.
Wed 5/141:55 pmMDW - MSP
Nonstop1h 40mDelta
Wed 5/2111:40 amMSP - MDW
Nonstop1h 35mDelta
Deal found 3/30$183

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 March 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 5/2

8:05 pm-9:49 pm

Nonstop1h 44m

Minneapolis St Paul

Sun 5/4

5:30 pm-7:09 pm

Nonstop1h 39m

$106

ChicagoMinneapolis

ORD - MSP

ORDMSP

Chicago O'Hare Intl

Fri 4/25

5:23 pm-12:35 am

1 stop7h 12m

Minneapolis St Paul

Sun 4/27

4:14 pm-5:53 pm

Nonstop1h 39m

$145

ChicagoMinneapolis

ORD - MSP

ORDMSP

Chicago O'Hare Intl

Fri 4/25

5:23 pm-12:35 am

1 stop7h 12m

Minneapolis St Paul

Mon 4/28

6:00 am-11:38 pm

1 stop17h 38m

$160

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

Fri 4/25

8:01 pm-12:35 am

1 stop28h 34m

Minneapolis St Paul

Mon 4/28

6:00 am-7:06 pm

1 stop13h 06m

$160

ChicagoMilwaukee

ORD - MKE

ORDMKE

Chicago O'Hare Intl

Wed 5/14

8:35 am-9:22 am

Nonstop0h 47m

Milwaukee-Mitchell

Wed 5/21

6:23 pm-7:23 pm

Nonstop1h 00m

$175

ChicagoMinneapolis

ORD - MSP

ORDMSP

Chicago O'Hare Intl

Sat 5/10

1:15 pm-2:48 pm

Nonstop1h 33m

Minneapolis St Paul

Sat 5/10

6:10 pm-7:45 pm

Nonstop1h 35m

$178

ChicagoMinneapolis

ORD - MSP

ORDMSP

Chicago O'Hare Intl

Sat 4/19

10:20 am-11:59 am

Nonstop1h 39m

Minneapolis St Paul

Sun 4/20

1:55 pm-3:29 pm

Nonstop1h 34m

$179

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

Mon 4/21

8:25 pm-9:43 pm

Nonstop1h 18m

Appleton Intl

Sat 4/26

6:20 pm-7:33 pm

Nonstop1h 13m

$179

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Thu 4/24

10:15 pm-11:20 pm

Nonstop1h 05m

Madison Truax Field

Mon 4/28

4:30 pm-5:42 pm

Nonstop1h 12m

$179

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

Sat 4/19

8:00 am-9:25 am

Nonstop1h 25m

Minneapolis St Paul

Wed 4/23

4:00 pm-5:30 pm

Nonstop1h 30m

$181

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/30

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 March 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 March 31, 2025.

The most flights from CHI to USWI are scheduled on a Sunday (45 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (25 on average).

Rainfall in Wisconsin by month

Plan your trip to Wisconsin by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Wisconsin ranges from 1.4 - 4.0 inches per month. June is typically the wettest month, when rainfall can reach 4.0 in. January is typically the driest time to visit Wisconsin when rainfall is around 1.4 in.

Temperature in Wisconsin by month

Plan your trip to Wisconsin by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Wisconsin, 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 21.2 F).

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 March 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
9,818 reviews

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Alaska Airlines
8.0
Very good
9,818 reviews
Alaska Airlines
8.0
Very good
9,818 reviews

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Southwest
8.0
Very good
4,275 reviews
Alaska Airlines
8.0
Very good
9,818 reviews

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Delta
8.0
Very good
7,899 reviews
Alaska Airlines
8.0
Very good
9,818 reviews

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Hawaiian Airlines
7.9
Good
2,344 reviews
Alaska Airlines
8.0
Very good
9,818 reviews

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
United Airlines
7.4
Good
8,614 reviews
Alaska Airlines
8.0
Very good
9,818 reviews

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Entertainment

7.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

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 Frontier and Delta, with prices starting from $79 and $90, 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 (90%), Qatar Airways (88%), Aer Lingus( 88%).

  • What are the cheapest flights from Chicago to Wisconsin?

    On average you can expect to pay $242 for a flight from Chicago to Wisconsin. The cheapest flight overall is $119 while the most popular route, (Chicago O'Hare Intl - Minneapolis St Paul) is currently priced at $116.

  • 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 March 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$179Average$322FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$184Average$369FlexibilityNo cancel feeOn-time71%
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