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$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 2/20. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — ORD
Dec 18 — Dec 251
Thu 12/18
Thu 12/25
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 November 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$77
(Kiwi.com)

One-way from

$49
(Southwest)

Popular in

January

Cheapest in

June

Average price

$334

Good round-trip deal

$296 or less

Good one-way deal

$169 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. 11% potential increase in price ($34 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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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 November 18, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/17. 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.
Fri 12/128:31 amMSP - ORD
Nonstop1h 45mFrontier
Mon 12/156:00 amORD - MSP
Nonstop1h 36mFrontier
Deal found 11/17$77
This Trip.com deal was found by Cheapflights users on 11/17. 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.
Mon 12/88:31 amMSP - ORD
Nonstop1h 45mMultiple Airlines
Fri 12/1211:48 amORD - MSP
Nonstop1h 42mMultiple Airlines
Deal found 11/17$78
This Kiwi.com deal was found by Cheapflights users on 11/18. 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 12/88:31 amMSP - ORD
Nonstop1h 45mFrontier
Mon 12/156:00 amORD - MSP
Nonstop1h 36mFrontier
Deal found 11/18$80
This Frontier deal was found by Cheapflights users on 11/18. 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.
Fri 12/58:31 amMSP - ORD
Nonstop1h 45mFrontier
Mon 12/86:00 amORD - MSP
Nonstop1h 36mFrontier
Deal found 11/18$81
This Super.com deal was found by Cheapflights users on 11/18. 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.
Sun 11/238:41 amMSP - ORD
Nonstop1h 35mFrontier
Wed 11/266:13 amORD - MSP
Nonstop1h 33mFrontier
Deal found 11/18$83
This Priceline deal was found by Cheapflights users on 11/18. 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.
Thu 12/1111:29 amMSP - ORD
1 stop10h 55mFrontier
Mon 12/156:00 amORD - MSP
Nonstop1h 36mFrontier
Deal found 11/18$84
This Booking.com deal was found by Cheapflights users on 11/17. 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.
Mon 12/228:00 amMSP - ORD
Nonstop1h 50mSun Country Air
Sun 12/288:19 amORD - MSP
Nonstop1h 39mSun Country Air
Deal found 11/17$85
This Super.com deal was found by Cheapflights users on 11/18. 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.
Mon 12/2210:09 pmMSP - ORD
Nonstop1h 45mFrontier
Fri 1/212:26 pmORD - MSP
Nonstop1h 36mFrontier
Deal found 11/18$91
This Sun Country Air deal was found by Cheapflights users on 11/18. 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.
Mon 11/248:54 amMSP - ORD
Nonstop1h 45mSun Country Air
Thu 11/279:20 amORD - MSP
Nonstop1h 42mSun Country Air
Deal found 11/18$92
This FlightHub deal was found by Cheapflights users on 11/18. 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.
Fri 12/195:00 pmMSP - ORD
Nonstop1h 38mSun Country Air
Fri 12/267:44 pmORD - MSP
Nonstop1h 39mSun Country Air
Deal found 11/18$93
This Southwest deal was found by Cheapflights users on 11/17. 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.
Mon 11/241:25 pmMSP - MDW
Nonstop1h 30mSouthwest
Thu 11/271:30 pmMDW - MSP
Nonstop1h 30mSouthwest
Deal found 11/17$97
This United Airlines deal was found by Cheapflights users on 11/17. 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 12/249:10 pmORD - STL
Nonstop1h 33mUnited Airlines
Thu 12/259:55 amSTL - ORD
Nonstop1h 35mUnited Airlines
Deal found 11/17$138

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 November 18, 2025.
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

Sun 2/15

9:51 am-11:32 am

Nonstop1h 41m

Chicago O'Hare Intl

Tue 2/17

8:05 pm-9:41 pm

Nonstop1h 36m

$97

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Sun 12/28

5:30 am-7:19 am

Nonstop1h 49m

Chicago O'Hare Intl

Thu 1/1

6:14 pm-7:53 pm

Nonstop1h 39m

$108

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Sat 12/13

6:12 am-7:56 am

Nonstop1h 44m

Chicago O'Hare Intl

Sun 12/14

9:40 pm-11:22 pm

Nonstop1h 42m

$115

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Mon 12/29

5:00 pm-6:38 pm

Nonstop1h 38m

Chicago O'Hare Intl

Thu 1/1

6:14 pm-7:53 pm

Nonstop1h 39m

$128

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Mon 11/24

8:54 am-10:39 am

Nonstop1h 45m

Chicago O'Hare Intl

Sun 11/30

9:18 am-11:00 am

Nonstop1h 42m

$135

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Mon 12/15

9:46 am-11:27 am

Nonstop1h 41m

Chicago O'Hare Intl

Wed 12/17

7:15 am-8:44 am

Nonstop1h 29m

$153

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Wed 1/14

7:45 am-2:15 pm

1 stop6h 30m

Chicago Midway

Sun 1/18

8:40 am-10:20 am

Nonstop1h 40m

$157

ChicagoSt. Louis

ORD - STL

ORDSTL

Chicago O'Hare Intl

Wed 12/24

4:01 pm-10:16 pm

1 stop6h 15m

Lambert-St Louis

Thu 12/25

6:29 am-12:54 pm

1 stop6h 25m

$157

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Fri 12/12

9:06 am-10:51 am

Nonstop1h 45m

Chicago O'Hare Intl

Sun 12/14

9:40 pm-11:22 pm

Nonstop1h 42m

$158

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Tue 12/9

4:30 pm-6:18 pm

Nonstop1h 48m

Chicago Midway

Sat 12/13

9:59 am-11:42 am

Nonstop1h 43m

$163

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/16

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, May is the cheapest month in which you can book a flight from Wisconsin to Illinois (average of $179). Flying from Wisconsin to Illinois in January is currently the most expensive (average of $198). 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 November 18, 2025.

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 afternoon could potentially save you up to 24% 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 December 16, 2024.

Travelers seeking maximum savings on their Wisconsin to Illinois flight should consider departing on Thursday mornings when fares are most often at their lowest. Sunday 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 November 18, 2025.

The most flights from USWI to USIL are scheduled on a Tuesday (55 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (29 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 November 18, 2025.
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
9,020 reviews

Comfort

7.3

Entertainment

7.1

Overall

7.4

Boarding

7.7

Crew

8.1

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
United Airlines
7.4
Good
9,020 reviews
United Airlines
7.4
Good
9,020 reviews

Comfort

7.3

Entertainment

7.1

Overall

7.4

Boarding

7.7

Crew

8.1

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
American Airlines
7.2
Good
11,046 reviews
United Airlines
7.4
Good
9,020 reviews

Comfort

7.3

Entertainment

7.1

Overall

7.4

Boarding

7.7

Crew

8.1

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000

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, Sun Country Air, and Southwest fly from Wisconsin to Illinois in about 1h 41m. The time it takes to get you to your destination can typically vary by up to 4h 49m. There are 333 mi between Wisconsin and Illinois. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Wisconsin to Illinois one-way?

    The cheapest airlines for a one-way flight from Wisconsin to Illinois are Southwest ($49), United Airlines ($49), and American Airlines ($49).

  • 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, May is the cheapest month in which you can book a flight from Wisconsin to Illinois (average of $179). Flying from Wisconsin to Illinois in January is currently the most expensive (average of $198). 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

Browse thousands of different options on Cheapflights for your next trip

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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 November 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$179Average$270FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$179Average$304FlexibilityNo cancel feeOn-time71%

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