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$59+ 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 7/6. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MKE
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$107
(Southwest)

One-way from

$59
(Sun Country Air)

Popular in

December

Cheapest in

April

Average price

$305

Good round-trip deal

$283 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. 25% potential increase in price ($96 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 June 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 June 12, 2025.

This Southwest deal was found by Cheapflights users on 6/12. 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.
Mon 8/257:40 amMDW - MSP
Nonstop1h 30mSouthwest
Wed 8/276:00 amMSP - MDW
1 stop3h 50mSouthwest
Deal found 6/12$107
This Cheapflightsfares deal was found by Cheapflights users on 6/10. 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 7/116:15 pmORD - MSP
Nonstop1h 40mSun Country Air
Sat 7/127:25 pmMSP - ORD
Nonstop1h 39mSun Country Air
Deal found 6/10$116
This Delta deal was found by Cheapflights users on 6/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/208:25 amORD - MSP
Nonstop1h 34mDelta
Sat 9/207:00 amMSP - ORD
Nonstop1h 39mDelta
Deal found 6/10$124
This Delta deal was found by Cheapflights users on 6/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/209:15 amMDW - MSP
Nonstop1h 38mDelta
Sat 9/207:00 amMSP - MDW
Nonstop1h 46mDelta
Deal found 6/10$124
This American Airlines deal was found by Cheapflights users on 6/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/167:21 amORD - MSP
Nonstop1h 42mAmerican Airlines
Sat 8/167:49 pmMSP - ORD
Nonstop1h 39mAmerican Airlines
Deal found 6/11$151
This United Airlines deal was found by Cheapflights users on 6/10. 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.
Wed 8/277:19 amORD - MSP
Nonstop1h 36mUnited Airlines
Mon 9/16:32 pmMSP - ORD
Nonstop1h 48mUnited Airlines
Deal found 6/10$157
This FlightHub deal was found by Cheapflights users on 6/10. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/185:40 amORD - MSP
1 stop5h 47mMultiple Airlines
Thu 8/213:48 pmMSP - ORD
Nonstop1h 42mMultiple Airlines
Deal found 6/10$159
This American Airlines deal was found by Cheapflights users on 6/10. 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.
Tue 7/812:16 pmORD - MKE
Nonstop0h 51mAmerican Airlines
Tue 7/156:27 amMKE - ORD
Nonstop1h 01mAmerican Airlines
Deal found 6/10$179
This United Airlines deal was found by Cheapflights users on 6/12. 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.
Mon 7/712:57 pmORD - ATW
Nonstop1h 11mUnited Airlines
Wed 7/301:05 pmATW - ORD
Nonstop1h 21mUnited Airlines
Deal found 6/12$179
This United Airlines deal was found by Cheapflights users on 6/10. 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.
Tue 7/812:45 pmORD - MSN
Nonstop1h 09mUnited Airlines
Tue 7/158:10 amMSN - ORD
Nonstop1h 10mUnited Airlines
Deal found 6/10$179
This United Airlines deal was found by Cheapflights users on 6/11. 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.
Thu 7/179:22 pmORD - EAU
Nonstop1h 23mUnited Airlines
Sun 7/205:30 amEAU - ORD
Nonstop1h 23mUnited Airlines
Deal found 6/11$180
This American Airlines deal was found by Cheapflights users on 6/9. 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 9/118:47 amORD - MSN
Nonstop1h 12mAmerican Airlines
Sat 9/137:58 amMSN - ORD
Nonstop1h 09mAmerican Airlines
Deal found 6/9$181

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 June 12, 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

Mon 8/25

7:40 am-9:10 am

Nonstop1h 30m

Minneapolis St Paul

Wed 8/27

6:00 am-9:50 am

1 stop3h 50m

$107

ChicagoMinneapolis

ORD - MSP

ORDMSP

Chicago O'Hare Intl

Fri 7/11

7:00 am-8:40 am

Nonstop1h 40m

Minneapolis St Paul

Mon 7/14

3:42 pm-5:21 pm

Nonstop1h 39m

$116

ChicagoMinneapolis

ORD - MSP

ORDMSP

Chicago O'Hare Intl

Wed 8/20

8:25 am-9:59 am

Nonstop1h 34m

Minneapolis St Paul

Sat 9/20

7:00 am-8:39 am

Nonstop1h 39m

$124

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

Wed 8/20

9:15 am-10:53 am

Nonstop1h 38m

Minneapolis St Paul

Sat 9/20

7:00 am-8:46 am

Nonstop1h 46m

$124

ChicagoMinneapolis

ORD - MSP

ORDMSP

Chicago O'Hare Intl

Sat 8/16

7:21 am-9:03 am

Nonstop1h 42m

Minneapolis St Paul

Sat 8/16

7:49 pm-9:28 pm

Nonstop1h 39m

$151

ChicagoMinneapolis

ORD - MSP

ORDMSP

Chicago O'Hare Intl

Wed 8/27

7:19 am-8:55 am

Nonstop1h 36m

Minneapolis St Paul

Mon 9/1

6:32 pm-8:20 pm

Nonstop1h 48m

$157

ChicagoMinneapolis

ORD - MSP

ORDMSP

Chicago O'Hare Intl

Mon 8/18

5:40 am-11:27 am

1 stop5h 47m

Minneapolis St Paul

Thu 8/21

3:48 pm-5:30 pm

Nonstop1h 42m

$159

ChicagoMilwaukee

ORD - MKE

ORDMKE

Chicago O'Hare Intl

Tue 7/8

12:16 pm-1:07 pm

Nonstop0h 51m

Milwaukee-Mitchell

Tue 7/15

6:27 am-7:28 am

Nonstop1h 01m

$179

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

Mon 7/7

12:57 pm-2:08 pm

Nonstop1h 11m

Appleton Intl

Wed 7/30

1:05 pm-2:26 pm

Nonstop1h 21m

$179

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Tue 7/8

12:45 pm-1:54 pm

Nonstop1h 09m

Madison Truax Field

Tue 7/15

8:10 am-9:20 am

Nonstop1h 10m

$179

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

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 June 12, 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 June 12, 2025.

The most flights from CHI to USWI are scheduled on a Wednesday (50 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (40 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 June 12, 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

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,287 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,946 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,790 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
JetBlue
7.3
Good
2,925 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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?

    $59 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 United Airlines, with prices starting from $59 and $76, 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%), Avianca (90%), Air Canada( 85%).

  • What are the cheapest flights from Chicago to Wisconsin?

    On average you can expect to pay $218 for a flight from Chicago to Wisconsin. The cheapest flight overall is $115 while the most popular route, (Chicago O'Hare Intl - Minneapolis St Paul) is currently priced at $97.

  • 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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$179Average$290FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$179Average$317FlexibilityNo cancel feeOn-time71%

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