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$69+ 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 7/23. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MKE
Jul 20 — Jul 271
Mon 7/20
Mon 7/27
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 June 20, 2026.

This Delta deal was found by Cheapflights users on 6/17. 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 7/158:27 am
ORD
-
MSP
Nonstop1h 35m
Delta
Wed 7/227:00 am
MSP
-
ORD
Nonstop1h 30m
Delta
Deal found 6/17$143
This United Airlines deal was found by Cheapflights users on 6/18. 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 9/36:59 am
ORD
-
MSP
Nonstop1h 40m
United Airlines
Wed 9/96:00 am
MSP
-
ORD
Nonstop1h 44m
United Airlines
Deal found 6/18$145
This Southwest deal was found by Cheapflights users on 6/17. 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 8/118:30 pm
MDW
-
MSP
Nonstop1h 30m
Southwest
Thu 8/133:45 pm
MSP
-
MDW
Nonstop1h 30m
Southwest
Deal found 6/17$145
This Super.com deal was found by Cheapflights users on 6/18. 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.
Sat 7/187:05 pm
ORD
-
MSP
Nonstop1h 46m
Sun Country Air
Wed 7/229:35 am
MSP
-
ORD
Nonstop1h 49m
Sun Country Air
Deal found 6/18$147
This Cheapflightsfares deal was found by Cheapflights users on 6/18. 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.
Thu 8/275:32 pm
ORD
-
MSP
Nonstop1h 36m
Sun Country Air
Mon 8/318:05 am
MSP
-
ORD
Nonstop1h 38m
Sun Country Air
Deal found 6/18$148
This Delta deal was found by Cheapflights users on 6/19. 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 8/83:00 pm
ORD
-
MSP
Nonstop1h 40m
Delta
Mon 8/108:10 pm
MSP
-
ORD
Nonstop1h 37m
Delta
Deal found 6/19$149
This Southwest deal was found by Cheapflights users on 6/19. 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 8/86:10 pm
MDW
-
MSP
Nonstop1h 30m
Southwest
Mon 8/103:45 pm
MSP
-
MDW
Nonstop1h 30m
Southwest
Deal found 6/19$149
This Trip.com deal was found by Cheapflights users on 6/18. 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.
Tue 7/2111:55 am
ORD
-
MSP
Nonstop1h 46m
Sun Country Air
Sat 7/253:15 pm
MSP
-
ORD
Nonstop1h 49m
Sun Country Air
Deal found 6/18$153
This Southwest deal was found by Cheapflights users on 6/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/44:40 pm
MDW
-
MSP
1 stop5h 45m
Southwest
Sat 8/85:30 am
MSP
-
MDW
Nonstop1h 25m
Southwest
Deal found 6/15$155
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 7/36:19 pm
ORD
-
MSP
Nonstop1h 46m
Sun Country Air
Sat 7/43:15 pm
MSP
-
ORD
Nonstop1h 49m
Sun Country Air
Deal found 6/18$157
This Sun Country Air deal was found by Cheapflights users on 6/17. 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.
Thu 7/237:25 am
ORD
-
MSP
Nonstop1h 46m
Sun Country Air
Sat 7/253:15 pm
MSP
-
ORD
Nonstop1h 49m
Sun Country Air
Deal found 6/17$158
This United Airlines deal was found by Cheapflights users on 6/17. 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 9/36:59 am
ORD
-
MSP
Nonstop1h 40m
United Airlines
Sun 9/66:00 am
MSP
-
ORD
Nonstop1h 44m
United Airlines
Deal found 6/17$159

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 June 20, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$143
(Delta)

One-way from

$69
(Cheapflightsfares)

Good round-trip deal

$200 or less

Good one-way deal

$88 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 June 20, 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

Sat 8/15

6:55 pm-8:33 pm

Nonstop1h 38m

Minneapolis St Paul

Mon 8/17

5:14 pm-6:59 pm

Nonstop1h 45m

$149

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

Sat 8/15

8:00 am-9:45 am

Nonstop1h 45m

Minneapolis St Paul

Mon 8/17

7:10 am-2:10 pm

1 stop7h 00m

$159

ChicagoMilwaukee

ORD - MKE

ORDMKE

Chicago O'Hare Intl

Tue 7/14

8:45 am-9:53 am

Nonstop1h 08m

Milwaukee-Mitchell

Tue 7/21

6:20 am-7:30 am

Nonstop1h 10m

$171

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Tue 7/14

9:00 pm-9:55 pm

Nonstop0h 55m

Milwaukee-Mitchell

Tue 7/21

4:10 pm-5:00 pm

Nonstop0h 50m

$171

ChicagoMilwaukee

ORD - MKE

ORDMKE

Chicago O'Hare Intl

Sat 8/8

5:45 pm-6:48 pm

Nonstop1h 03m

Milwaukee-Mitchell

Tue 8/11

5:00 am-6:10 am

Nonstop1h 10m

$181

ChicagoMinneapolis

ORD - MSP

ORDMSP

Chicago O'Hare Intl

Wed 7/15

8:27 am-10:02 am

Nonstop1h 35m

Minneapolis St Paul

Wed 7/22

6:04 am-10:37 am

1 stop4h 33m

$183

ChicagoMinneapolis

ORD - MSP

ORDMSP

Chicago O'Hare Intl

Sat 7/18

6:25 pm-8:08 pm

Nonstop1h 43m

Minneapolis St Paul

Tue 7/21

6:04 am-1:03 pm

1 stop6h 59m

$187

ChicagoMinneapolis

ORD - MSP

ORDMSP

Chicago O'Hare Intl

Tue 7/28

8:27 am-10:02 am

Nonstop1h 35m

Minneapolis St Paul

Tue 7/28

3:20 pm-4:59 pm

Nonstop1h 39m

$187

ChicagoMinneapolis

ORD - MSP

ORDMSP

Chicago O'Hare Intl

Sat 8/15

6:00 am-7:30 am

Nonstop1h 30m

Minneapolis St Paul

Mon 8/17

6:04 am-10:42 am

1 stop4h 38m

$189
Quickest round-trip

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Fri 9/4

8:40 pm-9:25 pm

Nonstop0h 45m

Milwaukee-Mitchell

Mon 9/7

5:45 am-6:30 am

Nonstop0h 45m

$205

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/15

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, January is the cheapest month in which you can book a flight from Chicago to Wisconsin (average of $179). Flying from Chicago to Wisconsin in May is currently the most expensive (average of $339). 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 20, 2026.

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 morning could potentially save you up to 26% on airfare.

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 20, 2026.

The most flights from CHI to USWI are scheduled on a Wednesday (58 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (30 on average).

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 June 13, 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.

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 20, 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
9,865 reviews

Entertainment

7.1

Food

6.6

Overall

7.4

Crew

8.1

Boarding

7.7

Comfort

7.3

Reviews

1 / 20
4.0
Okay

Dynasty,May 2026

LAX - EWR

The food wasn’t nice - Hosts were not that kind.
United Airlines
7.4
Good
9,865 reviews
United Airlines
7.4
Good
9,865 reviews

Entertainment

7.1

Food

6.6

Overall

7.4

Crew

8.1

Boarding

7.7

Comfort

7.3

Reviews

1 / 20
4.0
Okay

Dynasty,May 2026

LAX - EWR

The food wasn’t nice - Hosts were not that kind.
American Airlines
7.1
Good
11,715 reviews
United Airlines
7.4
Good
9,865 reviews

Entertainment

7.1

Food

6.6

Overall

7.4

Crew

8.1

Boarding

7.7

Comfort

7.3

Reviews

1 / 20
4.0
Okay

Dynasty,May 2026

LAX - EWR

The food wasn’t nice - Hosts were not that kind.

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 $183, United Airlines can have you in Wisconsin from Chicago in 1h 35m. 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: Japan Airlines (79%), Envoy Air (72%), Alaska Airlines( 69%).

  • What are the cheapest flights from Chicago to Wisconsin?

    On average you can expect to pay $243 for a flight from Chicago to Wisconsin. The cheapest flight overall is $98 while the most popular route, (Chicago O'Hare Intl - Minneapolis St Paul) is currently priced at $109.

  • 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, January is the cheapest month in which you can book a flight from Chicago to Wisconsin (average of $179). Flying from Chicago to Wisconsin in May is currently the most expensive (average of $339). 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 20, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$179Average$316FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$179Average$362FlexibilityNo cancel feeOn-time69%

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