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$59+ 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 8/19. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — CHI
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
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 July 29, 2025.

Round-trip from

$97
(Delta)

One-way from

$59
(Southwest)

Popular in

November

Cheapest in

June

Good round-trip deal

$233 or less

Good one-way deal

$175 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. 13% potential increase in price ($48 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($22 potential savings vs. average RT price).
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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 July 29, 2025.

This Delta deal was found by Cheapflights users on 7/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/237:14 amMSP - MDW
Nonstop1h 37mDelta
Tue 8/269:15 amMDW - MSP
Nonstop1h 38mDelta
Deal found 7/28$97
This Delta deal was found by Cheapflights users on 7/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/238:00 pmMSP - ORD
Nonstop1h 35mDelta
Tue 8/263:50 pmORD - MSP
Nonstop1h 49mDelta
Deal found 7/28$97
This Cheapflightsfares deal was found by Cheapflights users on 7/27. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/264:54 pmMSP - ORD
Nonstop1h 42mSun Country Air
Mon 9/297:33 pmORD - MSP
Nonstop1h 43mSun Country Air
Deal found 7/27$106
This Southwest deal was found by Cheapflights users on 7/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/233:25 pmMSP - MDW
1 stop3h 40mSouthwest
Tue 8/268:20 pmMDW - MSP
Nonstop1h 35mSouthwest
Deal found 7/28$107
This United Airlines deal was found by Cheapflights users on 7/27. 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.
Fri 8/296:30 pmMSP - ORD
Nonstop1h 47mUnited Airlines
Fri 8/299:50 pmORD - MSP
Nonstop1h 35mUnited Airlines
Deal found 7/27$118
This American Airlines deal was found by Cheapflights users on 7/27. 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 9/117:33 pmMSP - ORD
Nonstop1h 36mAmerican Airlines
Sun 9/147:19 amORD - MSP
Nonstop1h 30mAmerican Airlines
Deal found 7/27$123
This Mytrip deal was found by Cheapflights users on 7/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/239:22 amMSP - ORD
1 stop7h 04mMultiple Airlines
Mon 8/2510:10 amORD - MSP
Nonstop1h 47mMultiple Airlines
Deal found 7/28$132
This Southwest deal was found by Cheapflights users on 7/29. 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 8/196:20 amMSP - ORD
1 stop7h 50mSouthwest
Tue 8/263:10 pmORD - MSP
2 stops7h 15mSouthwest
Deal found 7/29$172
This Frontier deal was found by Cheapflights users on 7/26. 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.
Sat 8/24:14 pmMSP - MDW
1 stop6h 21mFrontier
Sat 8/96:20 amMDW - MSP
1 stop8h 31mFrontier
Deal found 7/26$178
This American Airlines deal was found by Cheapflights users on 7/27. 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 9/102:23 pmMKE - ORD
Nonstop1h 10mAmerican Airlines
Wed 9/175:55 pmORD - MKE
Nonstop0h 53mAmerican Airlines
Deal found 7/27$178
This United Airlines deal was found by Cheapflights users on 7/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/308:00 amDLH - ORD
Nonstop1h 55mUnited Airlines
Wed 9/38:12 pmORD - DLH
Nonstop1h 53mUnited Airlines
Deal found 7/28$179
This American Airlines deal was found by Cheapflights users on 7/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/306:02 amGRB - ORD
Nonstop1h 13mAmerican Airlines
Tue 9/28:05 amORD - GRB
Nonstop1h 07mAmerican Airlines
Deal found 7/29$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 July 29, 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 - MDW

MSPMDW

Minneapolis St Paul

Sat 8/23

4:05 pm-5:37 pm

Nonstop1h 32m

Chicago Midway

Tue 8/26

7:17 pm-9:00 pm

Nonstop1h 43m

$97

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Sat 8/23

8:00 pm-9:35 pm

Nonstop1h 35m

Chicago O'Hare Intl

Wed 9/3

3:50 pm-5:39 pm

Nonstop1h 49m

$97

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Fri 9/26

4:54 pm-6:36 pm

Nonstop1h 42m

Chicago O'Hare Intl

Mon 9/29

7:33 pm-9:16 pm

Nonstop1h 43m

$106

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Sat 8/23

3:25 pm-7:05 pm

1 stop3h 40m

Chicago Midway

Tue 8/26

8:20 pm-9:55 pm

Nonstop1h 35m

$107

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Fri 8/29

6:30 pm-8:17 pm

Nonstop1h 47m

Chicago O'Hare Intl

Fri 8/29

9:50 pm-11:25 pm

Nonstop1h 35m

$118

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Thu 9/11

7:33 pm-9:09 pm

Nonstop1h 36m

Chicago O'Hare Intl

Sun 9/14

7:19 am-8:49 am

Nonstop1h 30m

$123

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Sat 8/23

9:22 am-4:26 pm

1 stop7h 04m

Chicago O'Hare Intl

Mon 8/25

10:10 am-11:57 am

Nonstop1h 47m

$132

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Tue 8/19

6:20 am-2:10 pm

1 stop7h 50m

Chicago O'Hare Intl

Tue 8/26

3:10 pm-10:25 pm

2 stops7h 15m

$172

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Wed 9/10

2:23 pm-3:33 pm

Nonstop1h 10m

Chicago O'Hare Intl

Wed 9/17

5:55 pm-6:48 pm

Nonstop0h 53m

$178

DuluthChicago

DLH - ORD

DLHORD

Duluth Intl

Sat 8/30

8:00 am-9:55 am

Nonstop1h 55m

Chicago O'Hare Intl

Wed 9/3

8:12 pm-10:05 pm

Nonstop1h 53m

$179

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Showing 1-10 of 58 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 July 29, 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 July 29, 2025.

The most flights from USWI to CHI are scheduled on a Tuesday (52 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (31 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 July 29, 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

Comfort

7.8

Boarding

8.1

Crew

8.5

Entertainment

7.1

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Boarding

8.1

Crew

8.5

Entertainment

7.1

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Southwest
8.0
Very good
4,238 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Boarding

8.1

Crew

8.5

Entertainment

7.1

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Delta
8.0
Very good
7,977 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Boarding

8.1

Crew

8.5

Entertainment

7.1

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
United Airlines
7.4
Good
8,899 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Boarding

8.1

Crew

8.5

Entertainment

7.1

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Boarding

8.1

Crew

8.5

Entertainment

7.1

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.

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 $59 on Southwest. Other airlines that offer cheap prices include United Airlines from $62 and Sun Country Air from $63 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 Duluth 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 (75%), Copa Airlines (73%), Air Canada (72%).

  • What are the cheapest flights from Wisconsin to Chicago?

    Looking for the cheapest flight from Wisconsin to Chicago? While on average our users pay $1,014, our data indicates the cheapest price to be $98. The most popular route (Minneapolis St Paul - Chicago O'Hare Intl), is priced around $91.

  • 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
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 July 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$179Average$280FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$179Average$311FlexibilityNo cancel feeOn-time71%

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