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Illinois

$59+ Cheap flights from Wisconsin to Illinois

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 8/11. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — ORD
Jul 27 — Aug 31
Mon 7/27
Mon 8/3
1 adult, Economy
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Cheap flight deals from Wisconsin to Illinois

Cheapest flights from Wisconsin to Illinois
Explore the most affordable flight options available from Wisconsin to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 27, 2026.

This Southwest deal was found by Cheapflights users on 6/23. 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 7/215:25 am
MSP
-
MDW
Nonstop1h 30m
Southwest
Tue 7/285:10 pm
MDW
-
MSP
1 stop5h 40m
Southwest
Deal found 6/23$127
This Southwest deal was found by Cheapflights users on 6/24. 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 8/259:05 am
MSP
-
MDW
2 stops6h 55m
Southwest
Wed 8/262:20 pm
MDW
-
MSP
Nonstop1h 30m
Southwest
Deal found 6/24$132
This Southwest deal was found by Cheapflights users on 6/24. 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.
Sat 8/85:30 am
MSP
-
MDW
Nonstop1h 25m
Southwest
Sat 8/156:35 am
MDW
-
MSP
1 stop9h 35m
Southwest
Deal found 6/24$133
This United Airlines deal was found by Cheapflights users on 6/23. 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 6/3011:32 am
MSP
-
ORD
Nonstop1h 43m
United Airlines
Wed 7/17:00 am
ORD
-
MSP
Nonstop1h 41m
United Airlines
Deal found 6/23$137
This Southwest deal was found by Cheapflights users on 6/27. 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.
Sat 8/85:30 am
MSP
-
MDW
Nonstop1h 25m
Southwest
Sat 8/227:55 am
MDW
-
MSP
2 stops12h 10m
Southwest
Deal found 6/27$138
This Sun Country Air deal was found by Cheapflights users on 6/23. 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.
Wed 7/229:35 am
MSP
-
ORD
Nonstop1h 49m
Sun Country Air
Sat 7/256:05 pm
ORD
-
MSP
Nonstop1h 46m
Sun Country Air
Deal found 6/23$138
This Delta deal was found by Cheapflights users on 6/26. 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 10/17:05 am
MSP
-
MDW
Nonstop1h 43m
Delta
Sat 10/319:55 am
MDW
-
MSP
Nonstop1h 39m
Delta
Deal found 6/26$141
This United Airlines deal was found by Cheapflights users on 6/27. 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 9/108:00 am
MSP
-
ORD
Nonstop1h 44m
United Airlines
Sat 9/128:14 pm
ORD
-
MSP
Nonstop1h 38m
United Airlines
Deal found 6/27$141
This Southwest deal was found by Cheapflights users on 6/26. 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 8/266:15 am
MSP
-
MDW
Nonstop1h 25m
Southwest
Sat 8/296:10 pm
MDW
-
MSP
Nonstop1h 30m
Southwest
Deal found 6/26$142
This American Airlines deal was found by Cheapflights users on 6/26. 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.
Sat 8/87:02 am
MSP
-
ORD
Nonstop1h 52m
American Airlines
Mon 8/1010:40 pm
ORD
-
MSP
Nonstop1h 44m
American Airlines
Deal found 6/26$142
This Trip.com deal was found by Cheapflights users on 6/23. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/219:05 am
MSP
-
ORD
Nonstop1h 49m
Sun Country Air
Tue 7/2812:19 pm
ORD
-
MSP
Nonstop1h 46m
Sun Country Air
Deal found 6/23$143
This Delta deal was found by Cheapflights users on 6/25. 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 7/216:55 am
MSP
-
MDW
Nonstop1h 42m
Delta
Tue 7/281:49 pm
MDW
-
MSP
Nonstop1h 44m
Delta
Deal found 6/25$147

Find flight deals from Wisconsin to Illinois

Keep the following information in mind while searching for Wisconsin to Illinois flight deals. Data was last updated June 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$127
(Southwest)

One-way from

$59
(Southwest)

Good round-trip deal

$323 or less

Good one-way deal

$143 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 Illinois
Search Deals
One-way flight from Wisconsin to Illinois
Search Deals
Price to beat on a round-trip flight from Wisconsin to Illinois.
Search Deals
Price to beat on a one-way flight from Wisconsin to Illinois.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Wisconsin to Illinois 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 June 27, 2026.
Use the filters below to find and compare flights from Wisconsin to Illinois that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Wed 7/29

5:25 am-6:55 am

Nonstop1h 30m

Chicago Midway

Wed 7/29

5:20 pm-11:55 pm

1 stop6h 35m

$127

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Tue 8/11

8:00 am-1:55 pm

1 stop5h 55m

Chicago Midway

Tue 8/18

4:40 pm-10:25 pm

1 stop5h 45m

$137

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Wed 8/12

8:00 am-1:55 pm

1 stop5h 55m

Chicago Midway

Sat 8/15

6:35 am-11:50 am

1 stop5h 15m

$137

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Sat 8/8

5:30 am-6:55 am

Nonstop1h 25m

Chicago Midway

Mon 8/10

2:25 pm-3:55 pm

Nonstop1h 30m

$149

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Thu 11/5

12:25 pm-1:55 pm

Nonstop1h 30m

Chicago Midway

Thu 11/5

4:25 pm-6:00 pm

Nonstop1h 35m

$166

MinneapolisSt. Louis

MSP - STL

MSPSTL

Minneapolis St Paul

Mon 8/10

3:45 pm-10:05 pm

1 stop6h 20m

Lambert-St Louis

Tue 8/11

8:55 pm-10:25 pm

Nonstop1h 30m

$166

MinneapolisSt. Louis

MSP - STL

MSPSTL

Minneapolis St Paul

Thu 8/6

6:20 pm-10:05 pm

1 stop3h 45m

Lambert-St Louis

Sat 8/8

11:15 am-6:45 pm

1 stop7h 30m

$167

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Sat 7/25

6:04 am-12:38 pm

1 stop6h 34m

Chicago Midway

Sat 8/1

1:49 pm-3:33 pm

Nonstop1h 44m

$177

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Wed 8/26

9:00 am-1:08 pm

1 stop4h 08m

Chicago O'Hare Intl

Tue 9/1

6:44 pm-8:35 pm

Nonstop1h 51m

$177

Eau ClaireChicago

EAU - ORD

EAUORD

Eau Claire

Sat 9/5

5:00 am-6:30 am

Nonstop1h 30m

Chicago O'Hare Intl

Sun 9/13

12:20 pm-1:45 pm

Nonstop1h 25m

$180

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/22

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

Have a flexible travel schedule? Discover the best time to fly to Illinois 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 Illinois

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

Currently, January is the cheapest month in which you can book a flight from Wisconsin to Illinois (average of $179). Flying from Wisconsin to Illinois in July is currently the most expensive (average of $180). 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 IL?

Find hourly flight availability from Wisconsin to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 27, 2026.

One of the essential ways to save on airfare from Wisconsin to Illinois 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 33% on airfare.

Weekly flight availability from Wisconsin to Illinois

Explore weekly flight availability from Wisconsin to Illinois. 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 June 27, 2026.

The most flights from USWI to USIL are scheduled on a Friday (54 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (18 on average).

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

Use this chart to determine the cheapest time to fly round-trip from Wisconsin to Illinois. Price data was last updated on June 27, 2026.

Travelers seeking maximum savings on their Wisconsin to Illinois 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.

Reviews of airlines servicing Illinois

Get insights into the airlines that provide service to Illinois. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Illinois. Reviews last updated June 27, 2026.
See what other customers who have flown with United Airlines and American Airlines from Wisconsin to Illinois have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,896 reviews

Entertainment

7.1

Food

6.6

Boarding

7.7

Crew

8.1

Comfort

7.3

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
United Airlines
7.4
Good
9,896 reviews
United Airlines
7.4
Good
9,896 reviews

Entertainment

7.1

Food

6.6

Boarding

7.7

Crew

8.1

Comfort

7.3

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
American Airlines
7.1
Good
11,779 reviews
United Airlines
7.4
Good
9,896 reviews

Entertainment

7.1

Food

6.6

Boarding

7.7

Crew

8.1

Comfort

7.3

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

Related info for your journey

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

    Airlines like Southwest, Delta, and United Airlines fly from Wisconsin to Illinois in about 1h 30m. The time it takes to get you to your destination can typically vary by up to 2h 38m. There are 348 mi between Wisconsin and Illinois. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

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

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

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

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

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

    Currently, January is the cheapest month in which you can book a flight from Wisconsin to Illinois (average of $179). Flying from Wisconsin to Illinois in July is currently the most expensive (average of $180). 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

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Alternative routes for Wisconsin to Illinois

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 Illinois

Discover the top 2 airlines that operate flights from Wisconsin to Illinois. 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 June 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$168Average$297FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$179Average$259FlexibilityNo cancel feeOn-time69%

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