HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$58+ 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 12/6. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — CHI
oct. 11 — oct. 181
sáb. 10/11
sáb. 10/18
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Wisconsin to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 septiembre 11, 2025.

Round-trip from

$92
(Sun Country Air)

One-way from

$58
(Delta)

Popular in

November

Cheapest in

June

Average price

$239

Good round-trip deal

$297 or less

Good one-way deal

$102 or less
From Wisconsin to Chicago (CHI)
Search Deals
One-way flight from Wisconsin to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($56 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($19 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 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

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 septiembre 11, 2025.

This Priceline deal was found by Cheapflights users on 9/11. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/88:41 amMSP - ORD
Nonstop1h 35mFrontier
lun. 12/156:13 amORD - MSP
Nonstop1h 33mFrontier
Deal found 9/11$78
This Sun Country Air deal was found by Cheapflights users on 9/11. 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.
lun. 11/248:54 amMSP - ORD
Nonstop1h 45mSun Country Air
vie. 11/2811:00 amORD - MSP
Nonstop1h 42mSun Country Air
Deal found 9/11$92
This FlightHub deal was found by Cheapflights users on 9/9. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/64:42 pmMSP - ORD
Nonstop1h 38mSun Country Air
vie. 11/76:14 pmORD - MSP
Nonstop1h 42mSun Country Air
Deal found 9/9$93
This Booking.com deal was found by Cheapflights users on 9/9. 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.
vie. 10/244:36 pmMSP - ORD
Nonstop1h 39mSun Country Air
lun. 10/2711:41 amORD - MSP
Nonstop1h 43mSun Country Air
Deal found 9/9$95
This Frontier deal was found by Cheapflights users on 9/10. 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.
vie. 11/1412:54 pmMSP - ORD
1 stop12h 05mFrontier
lun. 12/156:13 amORD - MSP
Nonstop1h 33mFrontier
Deal found 9/10$96
This Cheapflightsfares deal was found by Cheapflights users on 9/9. 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.
vie. 12/58:41 amMSP - ORD
Nonstop1h 35mFrontier
lun. 12/86:13 amORD - MSP
Nonstop1h 33mFrontier
Deal found 9/9$97
This Delta deal was found by Cheapflights users on 9/11. 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.
sáb. 10/188:50 amMSP - MDW
Nonstop1h 40mDelta
mar. 10/217:10 pmMDW - MSP
Nonstop1h 39mDelta
Deal found 9/11$101
This Delta deal was found by Cheapflights users on 9/11. 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.
sáb. 10/41:43 pmMSP - ORD
Nonstop1h 30mDelta
mar. 12/26:00 amORD - MSP
Nonstop1h 36mDelta
Deal found 9/11$101
This American Airlines deal was found by Cheapflights users on 9/10. 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.
mié. 10/85:00 amMSP - ORD
Nonstop1h 32mAmerican Airlines
mié. 10/157:36 amORD - MSP
Nonstop1h 39mAmerican Airlines
Deal found 9/10$102
This Cheapflightsfares deal was found by Cheapflights users on 9/10. 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.
vie. 11/144:48 pmMSP - ORD
Nonstop1h 38mSun Country Air
dom. 11/166:08 pmORD - MSP
Nonstop1h 42mSun Country Air
Deal found 9/10$104
This Sun Country Air deal was found by Cheapflights users on 9/11. 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.
jue. 11/64:42 pmMSP - ORD
Nonstop1h 38mSun Country Air
dom. 11/96:08 pmORD - MSP
Nonstop1h 42mSun Country Air
Deal found 9/11$105
This Mytrip deal was found by Cheapflights users on 9/9. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/94:30 pmMSP - ORD
Nonstop1h 39mSun Country Air
lun. 10/1311:41 amORD - MSP
Nonstop1h 43mSun Country Air
Deal found 9/9$106

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 septiembre 11, 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

mar. 11/25

9:00 am-10:45 am

Nonstop1h 45m

Chicago O'Hare Intl

jue. 11/27

9:20 am-11:02 am

Nonstop1h 42m

$92

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

sáb. 10/4

8:00 am-9:43 am

Nonstop1h 43m

Chicago O'Hare Intl

mar. 12/2

7:15 am-8:44 am

Nonstop1h 29m

$101

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

lun. 10/13

9:00 am-10:39 am

Nonstop1h 39m

Chicago O'Hare Intl

jue. 10/16

8:21 pm-10:04 pm

Nonstop1h 43m

$105

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

jue. 11/27

1:29 pm-3:02 pm

Nonstop1h 33m

Chicago O'Hare Intl

mar. 12/2

11:03 am-12:36 pm

Nonstop1h 33m

$115

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

dom. 10/5

7:14 am-8:53 am

Nonstop1h 39m

Chicago Midway

mié. 10/8

9:20 am-11:02 am

Nonstop1h 42m

$117

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

dom. 10/5

6:55 am-8:25 am

Nonstop1h 30m

Chicago O'Hare Intl

mié. 10/8

6:08 am-7:35 am

Nonstop1h 27m

$117

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

mié. 10/15

3:22 pm-5:04 pm

Nonstop1h 42m

Chicago O'Hare Intl

dom. 10/19

5:37 pm-7:15 pm

Nonstop1h 38m

$117

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

mar. 11/25

9:00 am-10:45 am

Nonstop1h 45m

Chicago O'Hare Intl

sáb. 11/29

8:22 pm-10:04 pm

Nonstop1h 42m

$125

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

lun. 12/15

11:20 am-1:08 pm

Nonstop1h 48m

Chicago Midway

lun. 1/5

2:00 pm-3:40 pm

Nonstop1h 40m

$129

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

mar. 11/11

6:10 am-10:01 am

1 stop3h 51m

Chicago O'Hare Intl

mié. 11/12

6:00 am-7:36 am

Nonstop1h 36m

$130

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 60 results
1
2
3
...
6

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 septiembre 11, 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 septiembre 11, 2025.

The most flights from USWI to CHI are scheduled on a Thursday (52 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 33m. Sun Country Air provides one of the quickest options available for as low as $115. Wisconsin and Chicago are separated by a distance of 333 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 $65 on Delta. Other airlines that offer cheap prices include United Airlines from $67 and Frontier from $78 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 Appleton 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: Copa Airlines (66%), Avianca (66%), United Airlines (64%).

  • What are the cheapest flights from Wisconsin to Chicago?

    Looking for the cheapest flight from Wisconsin to Chicago? While on average our users pay $877, our data indicates the cheapest price to be $108. The most popular route (Minneapolis St Paul - Chicago O'Hare Intl), is priced around $70.

  • 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Wisconsin to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Dallas/Fort Worth to O'Hare Intl flights
John F Kennedy Intl to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
Newark to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Boston to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Baltimore to O'Hare Intl flights
Atlanta to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
John F Kennedy Intl to Midway flights
Seattle to O'Hare Intl flights
Ontario to O'Hare Intl flights
Denver to O'Hare Intl flights
Philadelphia to O'Hare Intl flights
Baltimore to Midway flights
Santa Ana to O'Hare Intl flights
Atlanta to Midway flights
LaGuardia to Midway flights
Los Angeles to Midway flights
Dulles Intl to Midway flights
Sky Harbor Intl to O'Hare Intl flights
Hobby to Midway flights
Hobby to O'Hare Intl flights
San Francisco to Midway flights
Burbank to O'Hare Intl flights
Newark to Midway flights
Austin to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Minneapolis to O'Hare Intl flights
Charlotte to O'Hare Intl flights
San Jose to O'Hare Intl flights
Portland to O'Hare Intl flights
Philadelphia to Midway flights
Minneapolis to Midway flights
Orlando to O'Hare Intl flights
San Diego to O'Hare Intl flights
Raleigh to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Boston to Midway flights
Denver to Midway flights
Reagan-National to Midway flights
Tampa to O'Hare Intl flights
Seattle to Midway flights
Love Field to O'Hare Intl flights
Miami to O'Hare Intl flights
Cleveland to O'Hare Intl flights
Oakland to O'Hare Intl flights

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 septiembre 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$179Average$282FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$179Average$313FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.