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$69+ 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 3/10. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — CHI
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$127
(Southwest)

One-way from

$69
(Southwest)

Good round-trip deal

$322 or less

Good one-way deal

$152 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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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 February 20, 2025.

This Southwest deal was found by Cheapflights users on 2/20. 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 4/34:10 pmMSP - MDW
Nonstop1h 30mSouthwest
Mon 4/74:15 pmMDW - MSP
1 stop6h 00mSouthwest
Deal found 2/20$127
This FlightHub deal was found by Cheapflights users on 2/20. 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.
Sun 6/15:30 pmMSP - ORD
Nonstop1h 39mSun Country Air
Thu 6/58:10 pmORD - MSP
Nonstop1h 40mSun Country Air
Deal found 2/20$128
This Mytrip deal was found by Cheapflights users on 2/20. 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.
Fri 4/411:00 amMSP - ORD
Nonstop1h 36mMultiple Airlines
Tue 4/86:25 pmORD - MSP
1 stop21h 10mMultiple Airlines
Deal found 2/20$129
This Frontier deal was found by Cheapflights users on 2/19. 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.
Mon 4/1410:55 amMSP - MDW
1 stop9h 19mFrontier
Wed 4/169:17 pmMDW - MSP
1 stop13h 17mFrontier
Deal found 2/19$130
This Mytrip deal was found by Cheapflights users on 2/20. 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.
Tue 4/16:00 amMSP - ORD
1 stop18h 15mFrontier
Tue 4/156:45 amORD - MSP
1 stop16h 48mFrontier
Deal found 2/20$131
This Delta deal was found by Cheapflights users on 2/20. 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.
Fri 3/217:59 amMSP - MDW
Nonstop1h 46mDelta
Mon 3/247:09 pmMDW - MSP
Nonstop1h 37mDelta
Deal found 2/20$132
This Delta deal was found by Cheapflights users on 2/19. 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.
Fri 4/118:15 pmMSP - ORD
Nonstop1h 30mDelta
Thu 4/176:35 amORD - MSP
Nonstop1h 35mDelta
Deal found 2/19$132
This United Airlines deal was found by Cheapflights users on 2/20. 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 3/146:42 pmMSP - ORD
Nonstop1h 43mUnited Airlines
Mon 3/247:10 amORD - MSP
Nonstop1h 33mUnited Airlines
Deal found 2/20$133
This FlightHub deal was found by Cheapflights users on 2/20. 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.
Wed 3/194:27 pmMSP - ORD
1 stop16h 17mSpirit Airlines
Tue 3/256:25 pmORD - MSP
1 stop19h 53mSpirit Airlines
Deal found 2/20$135
This United Airlines deal was found by Cheapflights users on 2/20. 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 10/315:30 amEAU - ORD
Nonstop1h 35mUnited Airlines
Sun 11/210:50 amORD - EAU
Nonstop1h 32mUnited Airlines
Deal found 2/20$180
This American Airlines deal was found by Cheapflights users on 2/20. 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.
Sun 3/167:00 amMSP - ORD
Nonstop1h 30mAmerican Airlines
Tue 3/189:40 pmORD - MSP
Nonstop1h 28mAmerican Airlines
Deal found 2/20$209
This American Airlines deal was found by Cheapflights users on 2/20. 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 6/34:37 pmATW - ORD
Nonstop1h 13mAmerican Airlines
Tue 6/179:40 amORD - ATW
Nonstop1h 12mAmerican Airlines
Deal found 2/20$227

Find flights from Wisconsin to Chicago within your budget

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 February 20, 2025.

Fly from

Wisconsin

Fly to

Chicago

Route

Depart

Return

Price

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Thu 4/3

6:30 am-9:55 am

1 stop3h 25m

Chicago Midway

Mon 4/7

7:15 am-8:45 am

Nonstop1h 30m

$127

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Sat 3/29

7:30 pm-9:06 pm

Nonstop1h 36m

Chicago O'Hare Intl

Thu 4/3

6:30 pm-8:10 pm

Nonstop1h 40m

$128

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Thu 4/3

4:00 pm-5:35 pm

Nonstop1h 35m

Chicago O'Hare Intl

Mon 4/7

8:33 pm-2:18 pm

1 stop17h 45m

$129

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Mon 4/14

10:55 am-8:14 pm

1 stop9h 19m

Chicago Midway

Wed 4/16

9:17 pm-10:34 am

1 stop13h 17m

$130

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Tue 4/1

6:00 am-12:15 am

1 stop18h 15m

Chicago O'Hare Intl

Tue 4/15

6:45 am-11:33 pm

1 stop16h 48m

$131

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Sat 4/5

6:35 pm-8:08 pm

Nonstop1h 33m

Chicago O'Hare Intl

Mon 4/7

6:15 am-7:48 am

Nonstop1h 33m

$132

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Fri 3/28

6:00 am-7:39 am

Nonstop1h 39m

Chicago O'Hare Intl

Mon 3/31

7:10 am-8:44 am

Nonstop1h 34m

$133

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Wed 3/19

4:27 pm-8:44 am

1 stop16h 17m

Chicago O'Hare Intl

Tue 3/25

6:25 pm-2:18 pm

1 stop19h 53m

$135

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Sat 4/5

4:59 pm-6:33 pm

Nonstop1h 34m

Chicago Midway

Sat 4/12

7:13 pm-8:50 pm

Nonstop1h 37m

$147

Eau ClaireChicago

EAU - ORD

EAUORD

Eau Claire

Sat 3/29

5:30 am-6:57 am

Nonstop1h 27m

Chicago O'Hare Intl

Sun 3/30

9:21 pm-10:45 pm

Nonstop1h 24m

$200

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

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.

Travel insights for flights from Wisconsin to Chicago

Get recent, data-driven insights about flights from Wisconsin to Chicago including ideal travel times, pricing trends, and more.

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 February 20, 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 February 20, 2025.

The most flights from USWI to CHI are scheduled on a Tuesday (45 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (39 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 February 20, 2025.
Read reviews from past customers who have flown Southwest, Alaska Airlines and Delta from Wisconsin to Chicago. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Boarding

8.2

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Boarding

8.2

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Alaska Airlines
8.0
Very good
9,692 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Boarding

8.2

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Boarding

8.2

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,766 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Boarding

8.2

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Allegiant Air
7.3
Good
765 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Boarding

8.2

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 $69 on Southwest. Other airlines that offer cheap prices include Frontier from $72 and Delta from $74 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: Republic Airways (95%), Qatar Airways (87%), Avianca (86%).

  • What are the cheapest flights from Wisconsin to Chicago?

    Looking for the cheapest flight from Wisconsin to Chicago? While on average our users pay $1,029, our data indicates the cheapest price to be $153. The most popular route (Minneapolis St Paul - Chicago O'Hare Intl), is priced around $114.

  • 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
New Buffalo
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 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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$178Average$271FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$178Average$324FlexibilityNo cancel feeOn-time71%
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