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$60+ 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 7/21. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — CHI
Jul 5 — Jul 121
Sat 7/5
Sat 7/12
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 June 30, 2025.

Round-trip from

$115
(Priceline)

One-way from

$60
(Booking.com)

Popular in

November

Cheapest in

March

Average price

$379

Good round-trip deal

$298 or less

Good one-way deal

$142 or less
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. 5% potential increase in price ($18 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($18 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 30, 2025.

This Priceline deal was found by Cheapflights users on 6/28. 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.
Sat 7/264:14 pmMSP - ORD
1 stop7h 15mFrontier
Sat 8/25:01 amORD - MSP
1 stop9h 50mFrontier
Deal found 6/28$115
This Priceline deal was found by Cheapflights users on 6/30. 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 7/313:42 pmMSP - ORD
Nonstop1h 39mMultiple Airlines
Sun 8/35:01 amORD - MSP
1 stop6h 22mMultiple Airlines
Deal found 6/30$116
This Southwest deal was found by Cheapflights users on 6/29. 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.
Thu 8/282:20 pmMSP - MDW
1 stop3h 10mSouthwest
Mon 9/17:30 amMDW - MSP
1 stop4h 00mSouthwest
Deal found 6/29$117
This Southwest deal was found by Cheapflights users on 6/29. 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 8/268:50 amMSP - ORD
1 stop5h 20mSouthwest
Wed 8/2712:40 pmORD - MSP
1 stop7h 15mSouthwest
Deal found 6/29$117
This Sun Country Air deal was found by Cheapflights users on 6/29. 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 7/239:42 amMSP - ORD
Nonstop1h 39mSun Country Air
Wed 7/308:10 pmORD - MSP
Nonstop1h 40mSun Country Air
Deal found 6/29$118
This Delta deal was found by Cheapflights users on 6/30. 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.
Sun 8/247:14 amMSP - MDW
Nonstop1h 37mDelta
Tue 8/267:17 pmMDW - MSP
Nonstop1h 43mDelta
Deal found 6/30$119
This Delta deal was found by Cheapflights users on 6/29. 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.
Sun 8/246:55 amMSP - ORD
Nonstop1h 29mDelta
Wed 8/276:10 amORD - MSP
Nonstop1h 28mDelta
Deal found 6/29$119
This American Airlines deal was found by Cheapflights users on 6/30. 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.
Tue 8/57:30 pmMSP - ORD
Nonstop1h 38mAmerican Airlines
Sat 8/910:12 pmORD - MSP
Nonstop1h 37mAmerican Airlines
Deal found 6/30$124
This Priceline deal was found by Cheapflights users on 6/30. 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.
Fri 9/126:45 amMSP - MDW
1 stop9h 08mFrontier
Mon 9/154:48 pmMDW - MSP
1 stop7h 28mFrontier
Deal found 6/30$161
This American Airlines deal was found by Cheapflights users on 6/28. 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.
Fri 8/86:26 pmGRB - ORD
Nonstop1h 13mAmerican Airlines
Sun 8/108:05 amORD - GRB
Nonstop1h 07mAmerican Airlines
Deal found 6/28$179
This American Airlines deal was found by Cheapflights users on 6/28. 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 8/217:49 pmMKE - ORD
Nonstop1h 04mAmerican Airlines
Sun 8/2411:40 amORD - MKE
Nonstop0h 56mAmerican Airlines
Deal found 6/28$179
This United Airlines deal was found by Cheapflights users on 6/29. 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.
Sat 8/232:41 pmATW - ORD
Nonstop1h 24mUnited Airlines
Sat 8/3010:54 amORD - ATW
Nonstop1h 11mUnited Airlines
Deal found 6/29$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 June 30, 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

Sat 7/26

4:14 pm-11:29 pm

1 stop7h 15m

Chicago O'Hare Intl

Sat 8/2

5:01 am-2:51 pm

1 stop9h 50m

$115

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Thu 7/31

3:42 pm-5:21 pm

Nonstop1h 39m

Chicago O'Hare Intl

Sun 8/3

5:01 am-11:23 am

1 stop6h 22m

$116

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Thu 8/28

2:20 pm-5:30 pm

1 stop3h 10m

Chicago Midway

Mon 9/1

5:25 am-11:00 am

1 stop5h 35m

$117

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Tue 8/26

8:50 am-2:10 pm

1 stop5h 20m

Chicago O'Hare Intl

Wed 8/27

12:40 pm-7:55 pm

1 stop7h 15m

$117

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Wed 7/23

9:42 am-11:21 am

Nonstop1h 39m

Chicago O'Hare Intl

Tue 7/29

12:08 pm-1:48 pm

Nonstop1h 40m

$118

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Sun 8/24

7:14 am-8:51 am

Nonstop1h 37m

Chicago Midway

Tue 8/26

7:17 pm-9:00 pm

Nonstop1h 43m

$119

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Sun 8/24

6:55 am-8:24 am

Nonstop1h 29m

Chicago O'Hare Intl

Mon 8/25

8:25 am-9:59 am

Nonstop1h 34m

$119

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Tue 8/5

7:30 pm-9:08 pm

Nonstop1h 38m

Chicago O'Hare Intl

Sat 8/9

10:12 pm-11:49 pm

Nonstop1h 37m

$124

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Fri 9/12

6:45 am-3:53 pm

1 stop9h 08m

Chicago Midway

Mon 9/15

4:48 pm-12:16 am

1 stop7h 28m

$161

AppletonChicago

ATW - ORD

ATWORD

Appleton Intl

Sat 8/23

2:41 pm-4:05 pm

Nonstop1h 24m

Chicago O'Hare Intl

Sat 8/30

10:54 am-12:05 pm

Nonstop1h 11m

$179

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/28

Showing 1-10 of 57 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 June 30, 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 June 30, 2025.

The most flights from USWI to CHI are scheduled on a Monday (51 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (35 on average).

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 June 30, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Southwest, and Delta from Wisconsin to Chicago by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Entertainment

7.1

Comfort

7.8

Food

7.1

Crew

8.5

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Entertainment

7.1

Comfort

7.8

Food

7.1

Crew

8.5

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,278 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Entertainment

7.1

Comfort

7.8

Food

7.1

Crew

8.5

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,969 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Entertainment

7.1

Comfort

7.8

Food

7.1

Crew

8.5

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,852 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Entertainment

7.1

Comfort

7.8

Food

7.1

Crew

8.5

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Entertainment

7.1

Comfort

7.8

Food

7.1

Crew

8.5

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 $60 on Sun Country Air. Other airlines that offer cheap prices include Frontier from $63 and Southwest from $64 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: Avianca (90%), Republic Airways (86%), United Airlines (84%).

  • What are the cheapest flights from Wisconsin to Chicago?

    Looking for the cheapest flight from Wisconsin to Chicago? While on average our users pay $3,770, our data indicates the cheapest price to be $124. The most popular route (Minneapolis St Paul - Chicago O'Hare Intl), is priced around $97.

  • 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
Lansing
Benton Harbor
Porter
Hammond
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 2 airlines flying from Wisconsin to Chicago

Discover the top 2 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 June 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$179Average$280FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$179Average$310FlexibilityNo cancel feeOn-time71%

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