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Wisconsin

$68+ 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 5/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MKE
Apr 16 — Apr 231
Thu 4/16
Thu 4/23
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 March 17, 2026.

This Southwest deal was found by Cheapflights users on 3/16. 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 4/2110:45 am
MDW
-
MSP
Nonstop1h 35m
Southwest
Wed 4/2210:05 am
MSP
-
MDW
Nonstop1h 30m
Southwest
Deal found 3/16$117
This Southwest deal was found by Cheapflights users on 3/12. 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.
Wed 4/82:40 pm
ORD
-
MSP
1 stop8h 25m
Southwest
Wed 4/158:40 am
MSP
-
ORD
1 stop6h 20m
Southwest
Deal found 3/12$122
This Southwest deal was found by Cheapflights users on 3/12. 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.
Wed 4/84:40 pm
MDW
-
MSP
1 stop5h 50m
Southwest
Wed 4/157:10 am
MSP
-
MDW
2 stops8h 35m
Southwest
Deal found 3/12$122
This United Airlines deal was found by Cheapflights users on 3/12. 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.
Wed 5/138:40 am
ORD
-
MSP
Nonstop1h 41m
United Airlines
Mon 5/188:00 am
MSP
-
ORD
Nonstop1h 38m
United Airlines
Deal found 3/12$127
This American Airlines deal was found by Cheapflights users on 3/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/1410:25 pm
ORD
-
MSP
Nonstop1h 34m
American Airlines
Wed 4/158:19 am
MSP
-
ORD
Nonstop1h 48m
American Airlines
Deal found 3/12$131
This Super.com deal was found by Cheapflights users on 3/13. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/247:35 pm
ORD
-
MSP
Nonstop1h 46m
Sun Country Air
Sun 4/264:12 pm
MSP
-
ORD
Nonstop1h 36m
Sun Country Air
Deal found 3/13$136
This Mytrip deal was found by Cheapflights users on 3/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/167:50 pm
ORD
-
MSP
Nonstop1h 46m
Sun Country Air
Mon 4/204:24 pm
MSP
-
ORD
Nonstop1h 36m
Sun Country Air
Deal found 3/15$137
This Southwest deal was found by Cheapflights users on 3/12. 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.
Sat 4/119:10 am
MDW
-
MSP
1 stop5h 00m
Southwest
Tue 4/146:15 pm
MSP
-
MDW
Nonstop1h 30m
Southwest
Deal found 3/12$137
This Southwest deal was found by Cheapflights users on 3/16. 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 4/212:40 pm
ORD
-
MSP
1 stop8h 25m
Southwest
Wed 4/227:10 am
MSP
-
ORD
1 stop5h 40m
Southwest
Deal found 3/16$142
This American Airlines deal was found by Cheapflights users on 3/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1612:24 pm
ORD
-
MSP
Nonstop1h 42m
American Airlines
Wed 5/208:19 am
MSP
-
ORD
Nonstop1h 48m
American Airlines
Deal found 3/12$144
This Gotogate deal was found by Cheapflights users on 3/15. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/177:27 pm
ORD
-
MSP
Nonstop1h 46m
Sun Country Air
Sun 4/194:24 pm
MSP
-
ORD
Nonstop1h 36m
Sun Country Air
Deal found 3/15$146
This Delta deal was found by Cheapflights users on 3/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/1312:30 pm
ORD
-
MSP
Nonstop1h 38m
Delta
Mon 5/185:38 pm
MSP
-
ORD
Nonstop1h 42m
Delta
Deal found 3/13$147

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 March 17, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$117
(United Airlines)

One-way from

$68
(Kiwi.com)

Good round-trip deal

$205 or less

Good one-way deal

$130 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
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 March 17, 2026.
Use the filters below to find and compare flights from Chicago to Wisconsin that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoMinneapolis

ORD - MSP

ORDMSP

Chicago O'Hare Intl

Wed 5/13

12:30 pm-2:08 pm

Nonstop1h 38m

Minneapolis St Paul

Sat 5/16

7:00 am-8:36 am

Nonstop1h 36m

$147

ChicagoMinneapolis

ORD - MSP

ORDMSP

Chicago O'Hare Intl

Fri 4/3

5:40 pm-9:41 pm

1 stop4h 01m

Minneapolis St Paul

Wed 4/8

6:10 pm-7:49 pm

Nonstop1h 39m

$172

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Tue 4/14

10:10 am-10:55 am

Nonstop0h 45m

Milwaukee-Mitchell

Tue 4/21

5:50 am-6:45 am

Nonstop0h 55m

$181
Quickest round-trip

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Sat 4/18

10:30 am-11:15 am

Nonstop0h 45m

Milwaukee-Mitchell

Sat 5/2

2:00 pm-2:45 pm

Nonstop0h 45m

$185

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

Sat 5/16

7:40 am-9:10 am

Nonstop1h 30m

Minneapolis St Paul

Wed 5/20

4:30 pm-9:50 pm

1 stop5h 20m

$187

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

Thu 4/16

4:05 pm-5:35 pm

Nonstop1h 30m

Minneapolis St Paul

Mon 4/20

3:40 pm-11:40 pm

1 stop8h 00m

$187

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Wed 4/15

10:10 am-10:55 am

Nonstop0h 45m

Milwaukee-Mitchell

Wed 4/22

8:00 am-11:35 am

1 stop3h 35m

$191

ChicagoMilwaukee

ORD - MKE

ORDMKE

Chicago O'Hare Intl

Sat 5/30

10:00 am-11:08 am

Nonstop1h 08m

Milwaukee-Mitchell

Tue 6/2

2:50 pm-4:01 pm

Nonstop1h 11m

$192

ChicagoMilwaukee

ORD - MKE

ORDMKE

Chicago O'Hare Intl

Fri 4/24

8:41 pm-9:49 pm

Nonstop1h 08m

Milwaukee-Mitchell

Wed 4/29

7:41 pm-8:50 pm

Nonstop1h 09m

$192

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Fri 4/24

10:10 am-10:55 am

Nonstop0h 45m

Milwaukee-Mitchell

Wed 4/29

5:50 am-6:45 am

Nonstop0h 55m

$192

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/12

Showing 1-10 of 60 resultsSorted by cheapest first
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6

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 March is currently the most expensive (average of $294). 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 17, 2026.

One of the essential ways to save on airfare from Chicago to Wisconsin is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the morning could potentially save you up to 8% 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 March 14, 2026.

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 evenings flights should be avoided if possible as fares are typically the most expensive at this time.

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 17, 2026.

The most flights from CHI to USWI are scheduled on a Tuesday (52 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (23 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 March 17, 2026.
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
9,431 reviews

Entertainment

7.1

Overall

7.4

Food

6.6

Comfort

7.3

Crew

8.1

Boarding

7.7

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
United Airlines
7.4
Good
9,431 reviews
United Airlines
7.4
Good
9,431 reviews

Entertainment

7.1

Overall

7.4

Food

6.6

Comfort

7.3

Crew

8.1

Boarding

7.7

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
American Airlines
7.1
Good
11,468 reviews
United Airlines
7.4
Good
9,431 reviews

Entertainment

7.1

Overall

7.4

Food

6.6

Comfort

7.3

Crew

8.1

Boarding

7.7

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family

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 $181, Delta can have you in Wisconsin from Chicago in 45m. There are 80 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: Lufthansa (70%), PSA Airlines (65%), United Airlines( 56%).

  • What are the cheapest flights from Chicago to Wisconsin?

    On average you can expect to pay $130 for a flight from Chicago to Wisconsin. The cheapest flight overall is $58 while the most popular route, (Chicago O'Hare Intl - Minneapolis St Paul) is currently priced at $137.

  • 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 March is currently the most expensive (average of $294). 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 17, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$179Average$258FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$179Average$345FlexibilityNo cancel feeOn-time69%

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