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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 4/10. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — CHI
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
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 December 18, 2025.

This United Airlines deal was found by Cheapflights users on 12/16. 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.
Wed 12/245:18 pmMSP - ORD
Nonstop1h 37mUnited Airlines
Thu 12/259:05 pmORD - MSP
Nonstop1h 39mUnited Airlines
Deal found 12/16$143
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/304:06 pmMSP - ORD
Nonstop1h 38mSun Country Air
Fri 1/211:51 amORD - MSP
Nonstop1h 39mSun Country Air
Deal found 12/16$154
This Orbitz deal was found by Cheapflights users on 12/16. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/262:57 pmMSP - ORD
Nonstop1h 45mFrontier
Thu 1/152:30 pmORD - MSP
1 stop9h 27mFrontier
Deal found 12/16$168
This United Airlines deal was found by Cheapflights users on 12/15. 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.
Wed 12/315:18 pmMSP - ORD
Nonstop1h 37mUnited Airlines
Tue 1/67:15 amORD - MSP
Nonstop1h 33mUnited Airlines
Deal found 12/15$169
This Kiwi.com deal was found by Cheapflights users on 12/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/2210:09 pmMSP - ORD
Nonstop1h 45mFrontier
Mon 1/57:00 amORD - MSP
1 stop13h 51mFrontier
Deal found 12/15$173
This United Airlines deal was found by Cheapflights users on 12/15. 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.
Wed 12/315:18 pmMSP - ORD
Nonstop1h 37mUnited Airlines
Thu 1/13:58 pmORD - MSP
Nonstop1h 31mUnited Airlines
Deal found 12/15$174
This Delta deal was found by Cheapflights users on 12/16. 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.
Wed 12/249:10 amMSP - MDW
Nonstop1h 56mDelta
Thu 12/2511:48 amMDW - MSP
Nonstop1h 44mDelta
Deal found 12/16$178
This Orbitz deal was found by Cheapflights users on 12/16. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/2910:09 pmMSP - ORD
Nonstop1h 45mMultiple Airlines
Thu 1/16:14 pmORD - MSP
Nonstop1h 39mMultiple Airlines
Deal found 12/16$179
This Super.com deal was found by Cheapflights users on 12/16. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/262:57 pmMSP - ORD
Nonstop1h 45mFrontier
Mon 12/297:38 pmORD - MSP
Nonstop1h 36mFrontier
Deal found 12/16$187
This Sun Country Air deal was found by Cheapflights users on 12/16. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/185:30 pmMSP - ORD
Nonstop1h 38mSun Country Air
Wed 12/3111:45 amORD - MSP
Nonstop1h 39mSun Country Air
Deal found 12/16$188
This Frontier deal was found by Cheapflights users on 12/16. 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.
Mon 12/2210:09 pmMSP - ORD
Nonstop1h 45mFrontier
Mon 12/297:38 pmORD - MSP
Nonstop1h 36mFrontier
Deal found 12/16$194
This American Airlines deal was found by Cheapflights users on 12/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/247:45 amMKE - ORD
Nonstop1h 18mAmerican Airlines
Mon 1/58:45 amORD - MKE
Nonstop1h 02mAmerican Airlines
Deal found 12/15$205

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 December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$92
(Booking.com)

One-way from

$59
(Mytrip)

Popular in

January

Cheapest in

June

Average price

$179

Good round-trip deal

$280 or less

Good one-way deal

$182 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. 19% potential increase in price ($68 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 11% potential price decrease ($30 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 December 18, 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 - MDW

MSPMDW

Minneapolis St Paul

Wed 1/14

4:50 pm-6:32 pm

Nonstop1h 42m

Chicago Midway

Wed 1/21

9:50 am-11:34 am

Nonstop1h 44m

$133

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Tue 1/13

2:30 pm-9:50 pm

1 stop7h 20m

Chicago Midway

Tue 1/20

8:40 am-10:20 am

Nonstop1h 40m

$143

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Sat 1/24

11:20 am-12:59 pm

Nonstop1h 39m

Chicago O'Hare Intl

Tue 1/27

8:18 pm-9:57 pm

Nonstop1h 39m

$152

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Sat 1/24

9:10 am-11:05 am

Nonstop1h 55m

Chicago Midway

Tue 1/27

1:49 pm-3:37 pm

Nonstop1h 48m

$152

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Tue 2/24

5:13 pm-6:54 pm

Nonstop1h 41m

Chicago O'Hare Intl

Thu 2/26

2:15 pm-3:50 pm

Nonstop1h 35m

$152

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Tue 2/24

11:22 am-1:07 pm

Nonstop1h 45m

Chicago Midway

Thu 2/26

9:50 am-11:32 am

Nonstop1h 42m

$152

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Tue 1/6

6:50 am-12:15 pm

1 stop5h 25m

Chicago O'Hare Intl

Wed 1/7

1:45 pm-8:35 pm

1 stop6h 50m

$153

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Mon 1/12

5:16 pm-6:55 pm

Nonstop1h 39m

Chicago O'Hare Intl

Sat 2/21

3:56 pm-5:28 pm

Nonstop1h 32m

$171

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Thu 1/22

7:05 am-9:08 am

Nonstop2h 03m

Chicago Midway

Mon 1/26

9:50 am-11:34 am

Nonstop1h 44m

$171

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Sat 1/24

2:30 pm-4:16 pm

Nonstop1h 46m

Chicago Midway

Mon 1/26

1:49 pm-3:37 pm

Nonstop1h 48m

$171

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/15

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 $184). 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 December 18, 2025.

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 31% 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 December 16, 2024.

Travelers seeking maximum savings on their Wisconsin to Chicago flight should consider departing on Thursday mornings 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 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 December 18, 2025.

The most flights from USWI to CHI are scheduled on a Thursday (47 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (12 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 39m. Delta provides one of the quickest options available for as low as $152. Wisconsin and Chicago are separated by a distance of 333 mi. This flight may include one or multiple stops.

  • 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 Madison Truax Field - 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: ANA (69%), Copa Airlines (67%), Air New Zealand (67%).

  • What are the cheapest flights from Wisconsin to Chicago?

    Looking for the cheapest flight from Wisconsin to Chicago? While on average our users pay $795, our data indicates the cheapest price to be $122. 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, 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 $184). 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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$179Average$299FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$179Average$259FlexibilityNo cancel feeOn-time69%

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