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Illinois

$49+ 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 5/12. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — ORD
Apr 9 — Apr 161
Thu 4/9
Thu 4/16
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 March 10, 2026.

This United Airlines deal was found by Cheapflights users on 3/5. 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 4/110:45 am
MKE
-
ORD
Nonstop1h 09m
United Airlines
Wed 4/810:30 am
ORD
-
MKE
Nonstop1h 02m
United Airlines
Deal found 3/5$97
This Southwest deal was found by Cheapflights users on 3/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/77:10 am
MSP
-
MDW
2 stops8h 35m
Southwest
Wed 4/89:05 pm
MDW
-
MSP
Nonstop1h 30m
Southwest
Deal found 3/9$112
This Southwest deal was found by Cheapflights users on 3/8. 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 4/1510:05 am
MSP
-
MDW
Nonstop1h 30m
Southwest
Sat 4/1810:35 am
MDW
-
MSP
Nonstop1h 30m
Southwest
Deal found 3/8$114
This United Airlines deal was found by Cheapflights users on 3/5. 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 4/26:50 am
MKE
-
ORD
Nonstop1h 09m
United Airlines
Thu 4/98:55 am
ORD
-
MKE
Nonstop1h 05m
United Airlines
Deal found 3/5$117
This Southwest deal was found by Cheapflights users on 3/8. 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 4/76:55 am
MSP
-
MDW
2 stops9h 40m
Southwest
Tue 4/144:50 pm
MDW
-
MSP
1 stop6h 15m
Southwest
Deal found 3/8$122
This Southwest deal was found by Cheapflights users on 3/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/216:55 am
MSP
-
ORD
1 stop8h 05m
Southwest
Tue 4/282:40 pm
ORD
-
MSP
1 stop8h 25m
Southwest
Deal found 3/9$122
This Southwest deal was found by Cheapflights users on 3/5. 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 4/15:15 am
MSP
-
MDW
Nonstop1h 30m
Southwest
Sat 4/47:40 am
MDW
-
MSP
Nonstop1h 30m
Southwest
Deal found 3/5$127
This Delta deal was found by Cheapflights users on 3/5. 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 4/218:00 pm
MSP
-
ORD
Nonstop1h 38m
Delta
Mon 4/277:09 pm
ORD
-
MSP
Nonstop1h 37m
Delta
Deal found 3/5$127
This Delta deal was found by Cheapflights users on 3/8. 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.
Sat 4/187:20 am
MSP
-
MDW
Nonstop1h 46m
Delta
Sat 4/252:12 pm
MDW
-
MSP
Nonstop1h 43m
Delta
Deal found 3/8$131
This Delta deal was found by Cheapflights users on 3/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/186:15 pm
MSP
-
ORD
Nonstop1h 37m
Delta
Sat 4/257:07 pm
ORD
-
MSP
Nonstop1h 37m
Delta
Deal found 3/9$131
This Super.com deal was found by Cheapflights users on 3/9. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/104:24 pm
MSP
-
ORD
Nonstop1h 36m
Sun Country Air
Mon 4/207:05 pm
ORD
-
MSP
Nonstop1h 46m
Sun Country Air
Deal found 3/9$136
This Kiwi.com deal was found by Cheapflights users on 3/5. 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.
Thu 4/234:42 pm
MSP
-
ORD
Nonstop1h 36m
Sun Country Air
Thu 4/308:06 pm
ORD
-
MSP
Nonstop1h 46m
Sun Country Air
Deal found 3/5$137

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 March 10, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$97
(United Airlines)

One-way from

$49
(Southwest)

Popular in

April

Cheapest in

January

Average price

$199

Good round-trip deal

$273 or less

Good one-way deal

$178 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
Highest demand for flights based on searches. 22% potential increase in price ($63 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
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 March 10, 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

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Sat 5/2

1:46 pm-2:55 pm

Nonstop1h 09m

Chicago O'Hare Intl

Sat 5/9

4:05 pm-5:07 pm

Nonstop1h 02m

$117

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Wed 4/8

3:15 pm-4:50 pm

Nonstop1h 35m

Chicago Midway

Sat 4/11

7:40 am-9:10 am

Nonstop1h 30m

$127

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Mon 5/4

5:20 pm-10:45 pm

1 stop5h 25m

Chicago Midway

Tue 5/5

4:50 pm-11:05 pm

1 stop6h 15m

$147

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Tue 4/21

10:00 am-11:35 am

Nonstop1h 35m

Chicago O'Hare Intl

Tue 4/28

12:42 pm-2:19 pm

Nonstop1h 37m

$157

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Thu 6/4

1:08 pm-2:50 pm

Nonstop1h 42m

Chicago O'Hare Intl

Mon 6/8

10:51 pm-12:33 am

Nonstop1h 42m

$157

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Mon 4/27

6:00 am-12:43 pm

1 stop6h 43m

Chicago Midway

Tue 4/28

7:16 pm-9:00 pm

Nonstop1h 44m

$167

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Wed 4/1

4:30 pm-9:55 pm

1 stop5h 25m

Chicago Midway

Thu 4/30

4:05 pm-5:35 pm

Nonstop1h 30m

$167

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Sat 5/2

5:56 pm-7:05 pm

Nonstop1h 09m

Chicago O'Hare Intl

Wed 5/6

11:00 pm-11:59 pm

Nonstop0h 59m

$167

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Fri 3/27

6:00 am-7:03 am

Nonstop1h 03m

Chicago O'Hare Intl

Sat 4/11

8:55 am-10:00 am

Nonstop1h 05m

$168

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Fri 5/8

7:10 pm-8:19 pm

Nonstop1h 09m

Chicago O'Hare Intl

Sat 5/9

7:40 pm-8:48 pm

Nonstop1h 08m

$168

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/9

Showing 1-10 of 60 resultsSorted by cheapest first
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6

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 September is currently the most expensive (average of $182). 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 March 10, 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 18% 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 February 21, 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 March 10, 2026.

The most flights from USWI to USIL are scheduled on a Monday (57 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (32 on average).

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 March 10, 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
9,409 reviews

Boarding

7.7

Crew

8.1

Food

6.6

Overall

7.4

Entertainment

7.1

Comfort

7.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
9,409 reviews
United Airlines
7.4
Good
9,409 reviews

Boarding

7.7

Crew

8.1

Food

6.6

Overall

7.4

Entertainment

7.1

Comfort

7.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
American Airlines
7.1
Good
11,413 reviews
United Airlines
7.4
Good
9,409 reviews

Boarding

7.7

Crew

8.1

Food

6.6

Overall

7.4

Entertainment

7.1

Comfort

7.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

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 United Airlines, Southwest, and Delta fly from Wisconsin to Illinois in about 1h 09m. The time it takes to get you to your destination can typically vary by up to 5h 34m. There are 67 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 September is currently the most expensive (average of $182). 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 March 10, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$179Average$288FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$179Average$250FlexibilityNo cancel feeOn-time69%

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