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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 3/24. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — CHI
Mar 19 — Mar 261
Thu 3/19
Thu 3/26
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 February 17, 2026.

This United Airlines deal was found by Cheapflights users on 2/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/166:00 am
MSP
-
ORD
Nonstop1h 37m
United Airlines
Sat 4/185:45 pm
ORD
-
MSP
Nonstop1h 38m
United Airlines
Deal found 2/15$128
This Southwest deal was found by Cheapflights users on 2/15. 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.
Thu 4/92:25 pm
MSP
-
MDW
Nonstop1h 25m
Southwest
Sat 4/116:25 pm
MDW
-
MSP
Nonstop1h 30m
Southwest
Deal found 2/15$131
This American Airlines deal was found by Cheapflights users on 2/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/168:08 am
MSP
-
ORD
Nonstop1h 48m
American Airlines
Sat 4/189:00 am
ORD
-
MSP
Nonstop1h 44m
American Airlines
Deal found 2/13$131
This Delta deal was found by Cheapflights users on 2/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/17:00 am
MSP
-
MDW
Nonstop1h 50m
Delta
Thu 4/29:30 am
MDW
-
MSP
Nonstop1h 37m
Delta
Deal found 2/15$134
This United Airlines deal was found by Cheapflights users on 2/16. 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.
Mon 3/96:45 pm
MSP
-
ORD
Nonstop1h 41m
United Airlines
Wed 3/112:15 pm
ORD
-
MSP
Nonstop1h 35m
United Airlines
Deal found 2/16$134
This American Airlines deal was found by Cheapflights users on 2/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/158:19 am
MSP
-
ORD
Nonstop1h 48m
American Airlines
Fri 4/1710:25 pm
ORD
-
MSP
Nonstop1h 34m
American Airlines
Deal found 2/17$136
This Kiwi.com deal was found by Cheapflights users on 2/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/1710:24 am
MSP
-
ORD
Nonstop1h 36m
Sun Country Air
Mon 4/207:05 pm
ORD
-
MSP
Nonstop1h 42m
Sun Country Air
Deal found 2/13$137
This Cheapflightsfares deal was found by Cheapflights users on 2/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/234:42 pm
MSP
-
ORD
Nonstop1h 36m
Sun Country Air
Mon 4/2710:16 am
ORD
-
MSP
Nonstop1h 42m
Sun Country Air
Deal found 2/13$138
This American Airlines deal was found by Cheapflights users on 2/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/165:18 am
MSP
-
ORD
Nonstop1h 46m
American Airlines
Sun 4/1910:21 pm
ORD
-
MSP
Nonstop1h 38m
American Airlines
Deal found 2/13$141
This American Airlines deal was found by Cheapflights users on 2/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/87:07 am
MSP
-
ORD
Nonstop1h 53m
American Airlines
Fri 4/1010:21 pm
ORD
-
MSP
Nonstop1h 38m
American Airlines
Deal found 2/13$143
This Southwest deal was found by Cheapflights users on 2/16. 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.
Wed 4/17:25 am
MSP
-
MDW
1 stop4h 15m
Southwest
Sat 4/47:40 am
MDW
-
MSP
Nonstop1h 30m
Southwest
Deal found 2/16$144
This Delta deal was found by Cheapflights users on 2/16. 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.
Sat 3/217:00 am
MSP
-
ORD
Nonstop1h 52m
Delta
Tue 3/248:30 pm
ORD
-
MSP
Nonstop1h 39m
Delta
Deal found 2/16$144

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 February 17, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$128
(United Airlines)

One-way from

$59
(Southwest)

Popular in

April

Cheapest in

January

Average price

$193

Good round-trip deal

$332 or less

Good one-way deal

$170 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
Highest demand for flights based on searches. 25% potential increase in price ($75 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
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 February 17, 2026.
Use the filters below to find and compare flights from Wisconsin to Chicago that are best for you.

Fly from

Wisconsin

Fly to

Chicago

Route

Depart

Return

Price

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Thu 4/16

8:13 am-9:50 am

Nonstop1h 37m

Chicago O'Hare Intl

Sat 4/18

4:05 pm-5:51 pm

Nonstop1h 46m

$128

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Thu 4/23

8:13 am-9:50 am

Nonstop1h 37m

Chicago O'Hare Intl

Sat 4/25

10:37 am-12:21 pm

Nonstop1h 44m

$128

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Thu 4/9

2:25 pm-3:50 pm

Nonstop1h 25m

Chicago Midway

Sat 4/11

6:25 pm-7:55 pm

Nonstop1h 30m

$131

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Sat 3/21

7:00 am-8:50 am

Nonstop1h 50m

Chicago Midway

Wed 3/25

2:05 pm-3:44 pm

Nonstop1h 39m

$134

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Wed 3/25

7:00 am-8:50 am

Nonstop1h 50m

Chicago Midway

Mon 3/30

7:20 pm-9:00 pm

Nonstop1h 40m

$134

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Wed 3/11

4:24 pm-6:00 pm

Nonstop1h 36m

Chicago O'Hare Intl

Thu 3/12

6:15 am-7:57 am

Nonstop1h 42m

$134

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Mon 3/16

6:10 pm-7:49 pm

Nonstop1h 39m

Chicago O'Hare Intl

Tue 3/17

6:15 am-7:57 am

Nonstop1h 42m

$134

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Sat 4/18

2:45 pm-8:05 pm

1 stop5h 20m

Chicago Midway

Tue 4/21

9:05 pm-10:35 pm

Nonstop1h 30m

$144

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Wed 3/25

9:55 am-11:36 am

Nonstop1h 41m

Chicago O'Hare Intl

Sat 3/28

2:15 pm-3:50 pm

Nonstop1h 35m

$151

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Fri 4/17

10:36 am-12:12 pm

Nonstop1h 36m

Chicago O'Hare Intl

Mon 4/20

5:11 am-12:55 pm

1 stop7h 44m

$154

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/15

Showing 1-10 of 60 results
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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 March is currently the most expensive (average of $183). 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 February 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 18% 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 February 17, 2026.

Travelers seeking maximum savings on their Wisconsin to Chicago flight should consider departing on Saturday 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 February 17, 2026.

The most flights from USWI to CHI are scheduled on a Monday (59 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (40 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 25m. United Airlines provides one of the quickest options available for as low as $131. Wisconsin and Chicago are separated by a distance of 348 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 Green Bay Austin-Straubel - 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: Republic Airways (83%), United Airlines (78%), Avianca (78%).

  • What are the cheapest flights from Wisconsin to Chicago?

    Looking for the cheapest flight from Wisconsin to Chicago? While on average our users pay $941, our data indicates the cheapest price to be $125. 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 March is currently the most expensive (average of $183). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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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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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 February 17, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$179Average$279FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$179Average$257FlexibilityNo cancel feeOn-time69%

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