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$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 4/7. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — ORD
Feb 14 — Feb 211
Sat 2/14
Sat 2/21
1 adult, Economy
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Cheap flight deals from Wisconsin to Illinois

Keep the following information in mind while searching for Wisconsin to Illinois flight deals. Data was last updated January 15, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$117
(Southwest)

One-way from

$59
(Delta)

Popular in

January

Cheapest in

June

Average price

$361

Good round-trip deal

$297 or less

Good one-way deal

$205 or less
Provider with most accurate pricing for Milwaukee-Mitchell-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Milwaukee-Mitchell-Chicago (CHI) flights.
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From Wisconsin to Illinois
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One-way flight from Wisconsin to Illinois
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Highest demand for flights based on searches. 9% potential increase in price ($27 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Price to beat on a round-trip flight from Wisconsin to Illinois.
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Price to beat on a one-way flight from Wisconsin to Illinois.
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Find 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 January 15, 2026.

This Southwest deal was found by Cheapflights users on 1/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/411:00 am
MSP
-
MDW
Nonstop1h 30m
Southwest
Wed 2/1112:00 pm
MDW
-
MSP
Nonstop1h 30m
Southwest
Deal found 1/14$117
This Delta deal was found by Cheapflights users on 1/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/283:30 pm
MSP
-
STL
Nonstop1h 32m
Delta
Tue 5/55:29 pm
STL
-
MSP
Nonstop1h 35m
Delta
Deal found 1/14$117
This United Airlines deal was found by Cheapflights users on 1/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/118:00 am
MSP
-
ORD
Nonstop1h 45m
United Airlines
Wed 2/187:25 am
ORD
-
MSP
Nonstop1h 30m
United Airlines
Deal found 1/14$117
This Booking.com deal was found by Cheapflights users on 1/14. 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 2/2010:54 am
MSP
-
ORD
Nonstop1h 33m
Sun Country Air
Sun 2/227:05 am
ORD
-
MSP
Nonstop1h 43m
Sun Country Air
Deal found 1/14$118
This Southwest deal was found by Cheapflights users on 1/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/114:20 pm
MSP
-
MDW
1 stop6h 30m
Southwest
Wed 3/187:55 am
MDW
-
MSP
Nonstop1h 35m
Southwest
Deal found 1/14$127
This Southwest deal was found by Cheapflights users on 1/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/107:45 am
MSP
-
STL
Nonstop1h 50m
Southwest
Tue 2/174:30 pm
STL
-
MSP
1 stop5h 50m
Southwest
Deal found 1/13$127
This Sun Country Air deal was found by Cheapflights users on 1/14. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/94:24 pm
MSP
-
ORD
Nonstop1h 39m
Sun Country Air
Fri 4/177:27 pm
ORD
-
MSP
Nonstop1h 44m
Sun Country Air
Deal found 1/14$128
This Kiwi.com deal was found by Cheapflights users on 1/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/264:12 pm
MSP
-
ORD
Nonstop1h 39m
Sun Country Air
Sun 5/38:06 pm
ORD
-
MSP
Nonstop1h 42m
Sun Country Air
Deal found 1/14$133
This Southwest deal was found by Cheapflights users on 1/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/46:50 am
MSP
-
ORD
1 stop5h 25m
Southwest
Wed 2/111:45 pm
ORD
-
MSP
1 stop6h 50m
Southwest
Deal found 1/14$137
This Booking.com deal was found by Cheapflights users on 1/14. 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.
Thu 5/145:30 pm
MSP
-
ORD
Nonstop1h 36m
Sun Country Air
Fri 5/158:06 pm
ORD
-
MSP
Nonstop1h 42m
Sun Country Air
Deal found 1/14$138
This Southwest deal was found by Cheapflights users on 1/15. 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.
Wed 2/116:05 am
MSP
-
MDW
1 stop5h 35m
Southwest
Wed 2/181:50 pm
MDW
-
MSP
1 stop8h 00m
Southwest
Deal found 1/15$143
This Southwest deal was found by Cheapflights users on 1/15. 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.
Tue 3/176:20 am
MSP
-
ORD
1 stop7h 35m
Southwest
Tue 3/242:40 pm
ORD
-
MSP
1 stop8h 50m
Southwest
Deal found 1/15$143

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 January 15, 2026.
Use the filters below to find and compare flights from Wisconsin to Illinois that are best for you.

Fly from

Wisconsin

Fly to

Illinois

Route

Depart

Return

Price

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Wed 2/11

6:55 am-8:40 am

Nonstop1h 45m

Chicago O'Hare Intl

Wed 2/18

8:50 am-10:28 am

Nonstop1h 38m

$117

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Tue 4/7

7:10 am-12:50 pm

1 stop5h 40m

Chicago O'Hare Intl

Tue 4/14

2:40 pm-11:05 pm

1 stop8h 25m

$143

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Thu 2/19

7:34 am-9:25 am

Nonstop1h 51m

Chicago O'Hare Intl

Tue 2/24

10:23 pm-11:56 pm

Nonstop1h 33m

$144

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Tue 2/10

4:55 pm-6:36 pm

Nonstop1h 41m

Chicago Midway

Sat 2/14

11:45 am-1:30 pm

Nonstop1h 45m

$144

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Sat 2/14

2:30 pm-4:14 pm

Nonstop1h 44m

Chicago Midway

Tue 2/17

1:49 pm-3:35 pm

Nonstop1h 46m

$144

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Thu 2/19

4:59 pm-6:40 pm

Nonstop1h 41m

Chicago Midway

Tue 2/24

7:20 pm-9:00 pm

Nonstop1h 40m

$144

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Wed 3/25

7:00 am-8:50 am

Nonstop1h 50m

Chicago Midway

Sat 3/28

9:30 am-11:07 am

Nonstop1h 37m

$144

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Wed 4/8

4:24 pm-6:00 pm

Nonstop1h 36m

Chicago O'Hare Intl

Mon 4/13

3:54 pm-5:30 pm

Nonstop1h 36m

$144

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Sat 4/11

6:10 pm-7:49 pm

Nonstop1h 39m

Chicago O'Hare Intl

Tue 4/14

3:54 pm-5:30 pm

Nonstop1h 36m

$144

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Thu 4/9

7:00 am-8:40 am

Nonstop1h 40m

Chicago O'Hare Intl

Tue 4/14

3:54 pm-5:30 pm

Nonstop1h 36m

$144

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/14

Showing 1-10 of 60 results
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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 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 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 January 15, 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 20% on airfare.

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 January 10, 2026.

Travelers seeking maximum savings on their Wisconsin to Illinois 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 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 January 15, 2026.

The most flights from USWI to USIL are scheduled on a Wednesday (45 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (38 on average).

How much does it cost to fly round-trip from Wisconsin to Illinois?

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 January 15, 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
9,164 reviews

Comfort

7.3

Crew

8.1

Boarding

7.7

Entertainment

7.1

Overall

7.4

Food

6.6

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
United Airlines
7.4
Good
9,164 reviews
United Airlines
7.4
Good
9,164 reviews

Comfort

7.3

Crew

8.1

Boarding

7.7

Entertainment

7.1

Overall

7.4

Food

6.6

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
American Airlines
7.2
Good
11,136 reviews
United Airlines
7.4
Good
9,164 reviews

Comfort

7.3

Crew

8.1

Boarding

7.7

Entertainment

7.1

Overall

7.4

Food

6.6

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family

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 Delta, Southwest, and American Airlines fly from Wisconsin to Illinois in about 1h 14m. The time it takes to get you to your destination can typically vary by up to 4h 26m. There are 258 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 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

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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 January 15, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$179Average$254FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$179Average$291FlexibilityNo cancel feeOn-time71%

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