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$49+ 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 6/24. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — CHI
Apr 29 — May 61
Tue 4/29
Tue 5/6
1 adult, Economy
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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 April 24, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$91
(American Airlines)

One-way from

$49
(Southwest)

Popular in

November

Cheapest in

March

Average price

$357

Good round-trip deal

$320 or less

Good one-way deal

$102 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 Chicago (CHI)
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One-way flight from Wisconsin to Chicago (CHI)
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Highest demand for flights based on searches. 3% potential increase in price ($10 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Price to beat on a round-trip flight from Wisconsin to Chicago (CHI).
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Price to beat on a one-way flight from Wisconsin to Chicago (CHI).
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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 April 24, 2025.

This American Airlines deal was found by Cheapflights users on 4/23. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/197:00 amMSP - ORD
Nonstop1h 48mAmerican Airlines
Mon 5/1910:28 pmORD - MSP
Nonstop1h 31mAmerican Airlines
Deal found 4/23$91
This Southwest deal was found by Cheapflights users on 4/23. 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 5/278:05 amMSP - MDW
Nonstop1h 30mSouthwest
Thu 5/295:20 amMDW - MSP
2 stops6h 20mSouthwest
Deal found 4/23$92
This Delta deal was found by Cheapflights users on 4/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/296:55 amMSP - ORD
Nonstop1h 29mDelta
Sat 5/316:24 amORD - MSP
Nonstop1h 30mDelta
Deal found 4/23$114
This Kissandfly.com deal was found by Cheapflights users on 4/23. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/233:36 pmMSP - ORD
Nonstop1h 39mSun Country Air
Mon 5/268:12 pmORD - MSP
Nonstop1h 48mSun Country Air
Deal found 4/23$115
This United Airlines deal was found by Cheapflights users on 4/22. 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 5/156:00 amMSP - ORD
Nonstop1h 37mUnited Airlines
Fri 5/239:50 pmORD - MSP
Nonstop1h 38mUnited Airlines
Deal found 4/22$125
This Delta deal was found by Cheapflights users on 4/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/244:05 pmMSP - MDW
Nonstop1h 35mDelta
Mon 6/309:21 amMDW - MSP
Nonstop1h 36mDelta
Deal found 4/23$137
This Mytrip deal was found by Cheapflights users on 4/23. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/74:07 pmMSP - ORD
1 stop8h 08mMultiple Airlines
Mon 6/96:09 pmORD - MSP
Nonstop1h 40mMultiple Airlines
Deal found 4/23$153
This CheapOair deal was found by Cheapflights users on 4/23. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/196:00 amMSP - MDW
1 stop13h 08mFrontier
Sat 5/242:44 pmMDW - MSP
1 stop20h 45mFrontier
Deal found 4/23$171
This CheapOair deal was found by Cheapflights users on 4/23. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/196:00 amMSP - ORD
1 stop17h 41mFrontier
Sat 5/246:00 amORD - MSP
1 stop18h 37mFrontier
Deal found 4/23$171
This American Airlines deal was found by Cheapflights users on 4/22. 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.
Wed 5/216:23 pmMKE - ORD
Nonstop1h 00mAmerican Airlines
Wed 5/284:50 pmORD - MKE
Nonstop0h 46mAmerican Airlines
Deal found 4/22$179
This American Airlines deal was found by Cheapflights users on 4/23. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/236:11 pmATW - ORD
Nonstop1h 15mAmerican Airlines
Sun 7/274:40 pmORD - ATW
Nonstop1h 00mAmerican Airlines
Deal found 4/23$179
This American Airlines deal was found by Cheapflights users on 4/23. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/153:28 pmMSN - ORD
Nonstop1h 01mAmerican Airlines
Sun 5/187:00 amORD - MSN
Nonstop1h 01mAmerican Airlines
Deal found 4/23$179

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 April 24, 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

Mon 5/19

7:00 am-8:48 am

Nonstop1h 48m

Chicago O'Hare Intl

Mon 5/19

10:28 pm-11:59 pm

Nonstop1h 31m

$91

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Tue 5/27

8:05 am-9:35 am

Nonstop1h 30m

Chicago Midway

Thu 5/29

5:20 am-11:40 am

2 stops6h 20m

$92

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Thu 5/29

6:55 am-8:24 am

Nonstop1h 29m

Chicago O'Hare Intl

Sat 5/31

6:24 am-7:54 am

Nonstop1h 30m

$114

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Fri 5/23

3:36 pm-5:15 pm

Nonstop1h 39m

Chicago O'Hare Intl

Mon 5/26

8:12 pm-10:00 pm

Nonstop1h 48m

$115

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Thu 5/15

6:00 am-7:37 am

Nonstop1h 37m

Chicago O'Hare Intl

Fri 5/23

9:50 pm-11:28 pm

Nonstop1h 38m

$125

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Thu 5/22

11:40 am-1:15 pm

Nonstop1h 35m

Chicago Midway

Sun 5/25

9:20 am-10:59 am

Nonstop1h 39m

$128

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Sat 6/7

4:07 pm-12:15 am

1 stop8h 08m

Chicago O'Hare Intl

Mon 6/9

6:09 pm-7:49 pm

Nonstop1h 40m

$153

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Mon 5/19

6:00 am-7:08 pm

1 stop13h 08m

Chicago Midway

Sat 5/24

2:44 pm-11:29 am

1 stop20h 45m

$171

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Mon 5/19

6:00 am-11:41 pm

1 stop17h 41m

Chicago O'Hare Intl

Sat 5/24

6:00 am-12:37 am

1 stop18h 37m

$171

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Wed 5/21

6:23 pm-7:23 pm

Nonstop1h 00m

Chicago O'Hare Intl

Wed 5/28

4:50 pm-5:36 pm

Nonstop0h 46m

$179

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/23

Showing 1-10 of 60 results
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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 April 24, 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 April 24, 2025.

The most flights from USWI to CHI are scheduled on a Monday (47 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (33 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated April 24, 2025.
Read reviews from past customers who have flown Alaska Airlines, Southwest and Delta from Wisconsin to Chicago. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,911 reviews

Entertainment

7.1

Food

7.1

Boarding

8.2

Crew

8.5

Comfort

7.9

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Alaska Airlines
8.0
Very good
9,911 reviews
Alaska Airlines
8.0
Very good
9,911 reviews

Entertainment

7.1

Food

7.1

Boarding

8.2

Crew

8.5

Comfort

7.9

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Southwest
8.0
Very good
4,287 reviews
Alaska Airlines
8.0
Very good
9,911 reviews

Entertainment

7.1

Food

7.1

Boarding

8.2

Crew

8.5

Comfort

7.9

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Delta
8.0
Very good
7,920 reviews
Alaska Airlines
8.0
Very good
9,911 reviews

Entertainment

7.1

Food

7.1

Boarding

8.2

Crew

8.5

Comfort

7.9

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
United Airlines
7.4
Good
8,685 reviews
Alaska Airlines
8.0
Very good
9,911 reviews

Entertainment

7.1

Food

7.1

Boarding

8.2

Crew

8.5

Comfort

7.9

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Allegiant Air
7.3
Good
734 reviews
Alaska Airlines
8.0
Very good
9,911 reviews

Entertainment

7.1

Food

7.1

Boarding

8.2

Crew

8.5

Comfort

7.9

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

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.

  • 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 $49 on Southwest. Other airlines that offer cheap prices include Sun Country Air from $58 and Delta from $69 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: Envoy Air (100%), Copa Airlines (85%), Avianca (78%).

  • What are the cheapest flights from Wisconsin to Chicago?

    Looking for the cheapest flight from Wisconsin to Chicago? While on average our users pay $849, our data indicates the cheapest price to be $119. The most popular route (Minneapolis St Paul - Chicago O'Hare Intl), is priced around $77.

  • 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 Wisconsin?

Book flights to Wisconsin if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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Alternative routes for Wisconsin to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Wisconsin to Chicago

Discover the top 3 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 April 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$179Average$321FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$180Average$282FlexibilityNo cancel feeOn-time69%
DeltaCheapest$198Average$208FlexibilityNo cancel feeOn-timeN/A

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