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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 11/13. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — CHI
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheap flight deals from Wisconsin to Chicago

Keep the following information in mind while searching for Wisconsin to Chicago flight deals. Data was last updated September 17, 2025.

Round-trip from

$92
(Sun Country Air)

One-way from

$59
(Southwest)

Popular in

November

Cheapest in

June

Average price

$239

Good round-trip deal

$297 or less

Good one-way deal

$113 or less
From Wisconsin to Chicago (CHI)
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One-way flight from Wisconsin to Chicago (CHI)
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Highest demand for flights based on searches. 13% potential increase in price ($45 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($20 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Wisconsin to Chicago (CHI).
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Price to beat on a one-way flight from Wisconsin to Chicago (CHI).
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Find 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 September 17, 2025.

This Sun Country Air deal was found by Cheapflights users on 9/17. 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.
Mon 12/295:00 pmMSP - ORD
Nonstop1h 38mSun Country Air
Tue 12/306:44 pmORD - MSP
Nonstop1h 39mSun Country Air
Deal found 9/17$92
This Southwest deal was found by Cheapflights users on 9/16. 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.
Thu 10/235:15 amMSP - MDW
Nonstop1h 30mSouthwest
Mon 10/277:45 amMDW - MSP
Nonstop1h 25mSouthwest
Deal found 9/16$97
This United Airlines deal was found by Cheapflights users on 9/17. 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.
Tue 10/146:00 amMSP - ORD
Nonstop1h 43mUnited Airlines
Wed 10/157:25 amORD - MSP
Nonstop1h 36mUnited Airlines
Deal found 9/17$97
This American Airlines deal was found by Cheapflights users on 9/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/235:00 amMSP - ORD
Nonstop1h 32mAmerican Airlines
Mon 10/277:36 amORD - MSP
Nonstop1h 39mAmerican Airlines
Deal found 9/16$98
This Delta deal was found by Cheapflights users on 9/17. 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.
Thu 10/306:59 amMSP - ORD
Nonstop1h 31mDelta
Mon 11/35:37 pmORD - MSP
Nonstop1h 38mDelta
Deal found 9/17$99
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/64:42 pmMSP - ORD
Nonstop1h 38mSun Country Air
Thu 11/67:20 pmORD - MSP
Nonstop1h 42mSun Country Air
Deal found 9/15$104
This Booking.com deal was found by Cheapflights users on 9/14. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/244:36 pmMSP - ORD
Nonstop1h 39mSun Country Air
Mon 10/2711:41 amORD - MSP
Nonstop1h 43mSun Country Air
Deal found 9/14$105
This Frontier deal was found by Cheapflights users on 9/16. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1411:29 amMSP - ORD
1 stop12h 42mFrontier
Fri 12/126:13 amORD - MSP
Nonstop1h 33mFrontier
Deal found 9/16$106
This Southwest deal was found by Cheapflights users on 9/17. 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 11/115:45 amMSP - MDW
2 stops6h 45mSouthwest
Sat 11/225:55 pmMDW - MSP
Nonstop1h 30mSouthwest
Deal found 9/17$112
This Southwest deal was found by Cheapflights users on 9/17. 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.
Thu 10/305:15 amMSP - MDW
Nonstop1h 30mSouthwest
Mon 11/311:25 amMDW - MSP
1 stop10h 20mSouthwest
Deal found 9/17$113
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/73:36 pmMSP - ORD
Nonstop1h 38mSun Country Air
Mon 11/1011:45 amORD - MSP
Nonstop1h 42mSun Country Air
Deal found 9/15$114
This Sun Country Air deal was found by Cheapflights users on 9/17. 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.
Fri 11/144:48 pmMSP - ORD
Nonstop1h 38mSun Country Air
Mon 11/1711:42 amORD - MSP
Nonstop1h 42mSun Country Air
Deal found 9/17$115

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 September 17, 2025.
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

Mon 11/24

8:54 am-10:39 am

Nonstop1h 45m

Chicago O'Hare Intl

Mon 12/1

9:18 am-11:00 am

Nonstop1h 42m

$92

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Tue 11/11

10:30 am-12:00 pm

Nonstop1h 30m

Chicago Midway

Sat 11/22

5:55 pm-7:25 pm

Nonstop1h 30m

$97

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Sat 11/8

8:50 am-10:30 am

Nonstop1h 40m

Chicago Midway

Sat 11/8

7:10 pm-8:49 pm

Nonstop1h 39m

$97

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Wed 10/22

6:00 am-7:43 am

Nonstop1h 43m

Chicago O'Hare Intl

Sat 10/25

8:51 am-10:27 am

Nonstop1h 36m

$97

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Sat 11/8

7:30 am-9:03 am

Nonstop1h 33m

Chicago O'Hare Intl

Sat 11/8

5:40 pm-7:12 pm

Nonstop1h 32m

$97

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Thu 10/9

6:00 am-7:43 am

Nonstop1h 43m

Chicago O'Hare Intl

Sat 10/11

2:15 pm-3:50 pm

Nonstop1h 35m

$97

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Wed 10/29

1:25 pm-2:55 pm

Nonstop1h 30m

Chicago O'Hare Intl

Tue 12/2

6:00 am-7:36 am

Nonstop1h 36m

$97

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Mon 10/20

6:10 pm-7:43 pm

Nonstop1h 33m

Chicago O'Hare Intl

Tue 10/21

11:02 am-12:35 pm

Nonstop1h 33m

$97

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Tue 10/7

6:00 am-9:55 am

1 stop3h 55m

Chicago Midway

Tue 10/7

8:35 pm-10:00 pm

Nonstop1h 25m

$107

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Thu 10/23

11:30 am-1:00 pm

Nonstop1h 30m

Chicago Midway

Mon 10/27

6:55 pm-11:50 pm

1 stop4h 55m

$107

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

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, August is the cheapest month in which you can book a flight from Wisconsin to Chicago (average of $245). Flying from Wisconsin to Chicago in March is currently the most expensive (average of $321). 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 September 17, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Wisconsin to Chicago as you normally would.

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 September 17, 2025.

The most flights from USWI to CHI are scheduled on a Monday (54 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (35 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 30m. Sun Country Air provides one of the quickest options available for as low as $97. Wisconsin and Chicago are separated by a distance of 348 mi. All flights are typically nonstop.

  • What are the cheapest airlines to fly from Wisconsin to Chicago one-way?

    One-way options have recently been found by users for as low as $59 on Southwest. Other airlines that offer cheap prices include Frontier from $93 and Delta from $99 one-way.

  • 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 Minneapolis St Paul - Chicago Greater Rockford.

  • 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: Copa Airlines (72%), Alaska Airlines (71%), Avianca (71%).

  • What are the cheapest flights from Wisconsin to Chicago?

    Looking for the cheapest flight from Wisconsin to Chicago? While on average our users pay $932, our data indicates the cheapest price to be $108. The most popular route (Minneapolis St Paul - Chicago O'Hare Intl), is priced around $92.

  • 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, August is the cheapest month in which you can book a flight from Wisconsin to Chicago (average of $245). Flying from Wisconsin to Chicago in March is currently the most expensive (average of $321). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$179Average$281FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$179Average$313FlexibilityNo cancel feeOn-time71%

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