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$59+ Cheap flights from Wisconsin to Chicago (CHI)

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 5/13. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — CHI
May 17 — May 241
Sun 5/17
Sun 5/24
1 adult, Economy
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Cheap flight deals from Wisconsin to Chicago

Cheapest flights from Wisconsin to Chicago
Explore the most affordable flight options available from Wisconsin to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 17, 2026.

This Southwest deal was found by Cheapflights users on 4/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/1210:05 am
MSP
-
MDW
Nonstop1h 30m
Southwest
Tue 5/194:40 pm
MDW
-
MSP
1 stop5h 50m
Southwest
Deal found 4/13$107
This Southwest deal was found by Cheapflights users on 4/16. 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 5/126:55 am
MSP
-
MDW
2 stops9h 40m
Southwest
Tue 5/129:05 pm
MDW
-
MSP
Nonstop1h 30m
Southwest
Deal found 4/16$112
This Southwest deal was found by Cheapflights users on 4/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/65:20 am
MSP
-
MDW
Nonstop1h 30m
Southwest
Wed 5/61:55 pm
MDW
-
MSP
1 stop8h 35m
Southwest
Deal found 4/14$113
This Kiwi.com deal was found by Cheapflights users on 4/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/101:25 pm
MSP
-
ORD
Nonstop1h 38m
Sun Country Air
Thu 11/197:32 pm
ORD
-
MSP
Nonstop1h 41m
Sun Country Air
Deal found 4/17$114
This Cheapflightsfares deal was found by Cheapflights users on 4/14. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/185:30 pm
MSP
-
ORD
Nonstop1h 36m
Sun Country Air
Mon 5/188:06 pm
ORD
-
MSP
Nonstop1h 44m
Sun Country Air
Deal found 4/14$115
This United Airlines deal was found by Cheapflights users on 4/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/1911:17 am
MSP
-
ORD
Nonstop1h 40m
United Airlines
Tue 5/267:05 am
ORD
-
MSP
Nonstop1h 41m
United Airlines
Deal found 4/16$116
This Southwest deal was found by Cheapflights users on 4/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/93:10 pm
MSP
-
MDW
1 stop6h 00m
Southwest
Wed 6/105:20 pm
MDW
-
MSP
1 stop6h 35m
Southwest
Deal found 4/13$117
This Delta deal was found by Cheapflights users on 4/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/25:38 pm
MSP
-
ORD
Nonstop1h 42m
Delta
Tue 6/912:27 pm
ORD
-
MSP
Nonstop1h 42m
Delta
Deal found 4/16$117
This Kiwi.com deal was found by Cheapflights users on 4/14. 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.
Tue 5/1210:55 am
MSP
-
ORD
Nonstop1h 36m
Multiple Airlines
Tue 5/199:37 pm
ORD
-
MSP
1 stop11h 42m
Multiple Airlines
Deal found 4/14$121
This Southwest deal was found by Cheapflights users on 4/16. 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 5/127:10 am
MSP
-
ORD
1 stop5h 40m
Southwest
Tue 5/122:40 pm
ORD
-
MSP
1 stop8h 25m
Southwest
Deal found 4/16$122
This Kiwi.com deal was found by Cheapflights users on 4/14. 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.
Mon 4/204:24 pm
MSP
-
ORD
Nonstop1h 36m
Sun Country Air
Thu 6/118:19 pm
ORD
-
MSP
Nonstop1h 43m
Sun Country Air
Deal found 4/14$124
This Cheapflightsfares deal was found by Cheapflights users on 4/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/285:30 pm
MSP
-
ORD
Nonstop1h 36m
Sun Country Air
Mon 6/18:06 pm
ORD
-
MSP
Nonstop1h 42m
Sun Country Air
Deal found 4/16$125

Find flight deals from Wisconsin to Chicago

Keep the following information in mind while searching for Wisconsin to Chicago flight deals. Data was last updated April 17, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$107
(Southwest)

One-way from

$59
(Delta)

Good round-trip deal

$352 or less

Good one-way deal

$202 or less
Provider with most accurate pricing for Milwaukee-Mitchell-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Milwaukee-Mitchell-Chicago (CHI) flights.
Search Deals
From Wisconsin to Chicago (CHI)
Search Deals
One-way flight from Wisconsin to Chicago (CHI)
Search Deals
Price to beat on a round-trip flight from Wisconsin to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Wisconsin to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Wisconsin to Chicago 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 April 17, 2026.
Use the filters below to find and compare flights from Wisconsin to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Thu 5/14

5:20 am-6:50 am

Nonstop1h 30m

Chicago Midway

Thu 5/21

8:05 am-9:40 am

Nonstop1h 35m

$177

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Thu 5/28

7:00 am-8:42 am

Nonstop1h 42m

Chicago Midway

Sat 5/30

7:13 pm-8:55 pm

Nonstop1h 42m

$177

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Sat 5/16

3:15 pm-4:51 pm

Nonstop1h 36m

Chicago O'Hare Intl

Mon 5/18

8:05 pm-9:50 pm

Nonstop1h 45m

$177

Eau ClaireChicago

EAU - ORD

EAUORD

Eau Claire

Mon 5/11

2:43 pm-4:09 pm

Nonstop1h 26m

Chicago O'Hare Intl

Wed 5/13

9:55 pm-11:19 pm

Nonstop1h 24m

$180

Eau ClaireChicago

EAU - ORD

EAUORD

Eau Claire

Tue 5/5

9:30 am-10:56 am

Nonstop1h 26m

Chicago O'Hare Intl

Tue 5/5

4:40 pm-6:09 pm

Nonstop1h 29m

$180

Eau ClaireChicago

EAU - ORD

EAUORD

Eau Claire

Fri 10/2

2:45 pm-4:18 pm

Nonstop1h 33m

Chicago O'Hare Intl

Sat 10/3

12:35 pm-2:05 pm

Nonstop1h 30m

$180

Eau ClaireChicago

EAU - ORD

EAUORD

Eau Claire

Tue 5/19

9:30 am-10:56 am

Nonstop1h 26m

Chicago O'Hare Intl

Thu 5/21

12:35 pm-2:05 pm

Nonstop1h 30m

$180

Eau ClaireChicago

EAU - ORD

EAUORD

Eau Claire

Wed 7/15

5:00 am-6:27 am

Nonstop1h 27m

Chicago O'Hare Intl

Mon 7/27

12:35 pm-2:05 pm

Nonstop1h 30m

$180

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Mon 5/11

6:10 am-1:01 pm

1 stop6h 51m

Chicago O'Hare Intl

Tue 5/12

8:05 pm-9:50 pm

Nonstop1h 45m

$192

Eau ClaireChicago

EAU - ORD

EAUORD

Eau Claire

Thu 9/24

5:30 am-7:05 am

Nonstop1h 35m

Chicago O'Hare Intl

Sun 9/27

9:30 pm-10:52 pm

Nonstop1h 22m

$200

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/12

Showing 1-10 of 60 resultsSorted by cheapest first
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Best time to book a flight from Wisconsin to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Wisconsin 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 Wisconsin to Chicago

What is the cheapest month to book a flight from Wisconsin to Chicago?

Currently, January is the cheapest month in which you can book a flight from Wisconsin to Chicago (average of $179). Flying from Wisconsin to Chicago in January is currently the most expensive (average of $179). 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 WI to CHI?

Find hourly flight availability from Wisconsin to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 17, 2026.

One of the essential ways to save on airfare from Wisconsin to Chicago is to remain as flexible as possible. Flights that are in the evening tend to be the most expensive. A flight in the morning could potentially save you up to 43% on airfare.

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

Use this chart to determine the cheapest time to fly round-trip from Wisconsin to Chicago. Price data was last updated on April 11, 2026.

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

Weekly flight availability from Wisconsin to Chicago

Explore weekly flight availability from Wisconsin to Chicago. 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 April 17, 2026.

The most flights from USWI to CHI are scheduled on a Friday (71 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (52 on average).

Related info for your journey

Find useful and relevant information for your journey from Wisconsin to Chicago. 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 Wisconsin to Chicago?

    A quick flight from Wisconsin to Chicago can take about 1h 26m. Delta provides one of the quickest options available for as low as $180. Wisconsin and Chicago are separated by a distance of 268 mi. All flights are typically nonstop.

  • What are the most popular routes from Wisconsin to Chicago?

    The most popular route from Wisconsin to Chicago is Minneapolis St Paul - Chicago O'Hare Intl. You may also consider Minneapolis St Paul - Chicago Midway or Duluth Intl - Chicago O'Hare Intl.

  • What are the most reliable airlines from Wisconsin to Chicago?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Wisconsin to Chicago on time: Air Canada (62%), Air New Zealand (62%), Copa Airlines (60%).

  • What are the cheapest flights from Wisconsin to Chicago?

    Looking for the cheapest flight from Wisconsin to Chicago? While on average our users pay $697, our data indicates the cheapest price to be $145. The most popular route (Minneapolis St Paul - Chicago O'Hare Intl), is priced around $91.

  • Can I find deals for flights from Wisconsin to Chicago that include hotel bookings?

    Yes. In addition to deals on Wisconsin to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Wisconsin to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Wisconsin to Chicago.

  • Can I find deals for business class flights from Wisconsin to Chicago?

    Yes. Cheapflights offers flight deals from Wisconsin to Chicago 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 Wisconsin to Chicago?

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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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Alternative routes for Wisconsin to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Newark to St. Louis flights
Minneapolis to Midway flights
LaGuardia to St. Louis flights
Philadelphia to Midway flights
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Orlando to Midway flights
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Denver to Midway flights
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Top 2 airlines flying from Wisconsin to Chicago

Discover the top 2 airlines that operate flights from Wisconsin to Chicago. 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 April 17, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$168Average$276FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$179Average$255FlexibilityNo cancel feeOn-time69%

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