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$52+ 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 6/25. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — CHI
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$116
(Cheapflightsfares)

One-way from

$52
(eDestinos)

Popular in

November

Cheapest in

March

Average price

$303

Good round-trip deal

$313 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 ($12 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 May 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 May 1, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/3010:48 amMSP - ORD
Nonstop1h 39mSun Country Air
Mon 6/28:05 pmORD - MSP
Nonstop1h 44mSun Country Air
Deal found 4/30$116
This Southwest deal was found by Cheapflights users on 4/29. 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.
Wed 5/2812:35 pmMSP - MDW
Nonstop1h 30mSouthwest
Wed 5/285:05 pmMDW - MSP
Nonstop1h 30mSouthwest
Deal found 4/29$159
This Priceline deal was found by Cheapflights users on 4/30. 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.
Sat 6/74:07 pmMSP - ORD
1 stop8h 08mMultiple Airlines
Sun 6/86:30 amORD - MSP
Nonstop1h 40mMultiple Airlines
Deal found 4/30$160
This American Airlines deal was found by Cheapflights users on 4/30. 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.
Fri 6/65:53 pmGRB - ORD
Nonstop1h 18mAmerican Airlines
Sun 6/84:08 pmORD - GRB
Nonstop0h 58mAmerican Airlines
Deal found 4/30$179
This Delta deal was found by Cheapflights users on 4/30. 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.
Wed 5/283:15 pmMSP - ORD
Nonstop1h 30mDelta
Fri 5/308:12 pmORD - MSP
Nonstop1h 48mDelta
Deal found 4/30$179
This American Airlines deal was found by Cheapflights users on 4/30. 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.
Thu 6/2610:15 amMKE - ORD
Nonstop1h 02mAmerican Airlines
Sun 7/61:51 pmORD - MKE
Nonstop0h 48mAmerican Airlines
Deal found 4/30$179
This American Airlines deal was found by Cheapflights users on 4/30. 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.
Wed 7/239:44 amATW - ORD
Nonstop1h 10mAmerican Airlines
Sun 7/274:40 pmORD - ATW
Nonstop1h 00mAmerican Airlines
Deal found 4/30$179
This American Airlines deal was found by Cheapflights users on 4/30. 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.
Thu 5/295:09 amMSN - ORD
Nonstop1h 01mAmerican Airlines
Thu 6/58:16 amORD - MSN
Nonstop1h 04mAmerican Airlines
Deal found 4/30$179
This United Airlines deal was found by Cheapflights users on 4/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/145:30 amEAU - ORD
Nonstop1h 23mUnited Airlines
Sat 6/2112:25 pmORD - EAU
Nonstop1h 29mUnited Airlines
Deal found 4/30$180
This Delta deal was found by Cheapflights users on 4/29. 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.
Thu 5/2211:40 amMSP - MDW
Nonstop1h 35mDelta
Sun 5/259:20 amMDW - MSP
Nonstop1h 39mDelta
Deal found 4/29$181
This American Airlines deal was found by Cheapflights users on 4/29. 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.
Tue 5/209:20 amMSP - ORD
Nonstop1h 35mAmerican Airlines
Wed 5/211:15 pmORD - MSP
Nonstop1h 33mAmerican Airlines
Deal found 4/29$183
This Frontier deal was found by Cheapflights users on 4/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/144:13 pmMSP - MDW
1 stop6h 15mFrontier
Sat 6/216:20 amMDW - MSP
1 stop8h 41mFrontier
Deal found 4/30$184

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 May 1, 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

Fri 5/30

10:48 am-12:27 pm

Nonstop1h 39m

Chicago O'Hare Intl

Mon 6/2

8:05 pm-9:49 pm

Nonstop1h 44m

$116

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Wed 5/28

12:35 pm-2:05 pm

Nonstop1h 30m

Chicago Midway

Wed 5/28

5:05 pm-6:35 pm

Nonstop1h 30m

$159

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Sat 6/7

4:07 pm-12:15 am

1 stop8h 08m

Chicago O'Hare Intl

Sun 6/8

6:30 am-8:10 am

Nonstop1h 40m

$160

Green BayChicago

GRB - ORD

GRBORD

Green Bay Austin-Straubel

Fri 6/6

5:53 pm-7:11 pm

Nonstop1h 18m

Chicago O'Hare Intl

Sun 6/8

4:08 pm-5:06 pm

Nonstop0h 58m

$179

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Wed 5/28

3:15 pm-4:45 pm

Nonstop1h 30m

Chicago O'Hare Intl

Fri 5/30

8:12 pm-10:00 pm

Nonstop1h 48m

$179

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Thu 6/26

10:15 am-11:17 am

Nonstop1h 02m

Chicago O'Hare Intl

Sun 7/6

1:51 pm-2:39 pm

Nonstop0h 48m

$179

AppletonChicago

ATW - ORD

ATWORD

Appleton Intl

Sat 5/24

5:40 am-6:52 am

Nonstop1h 12m

Chicago O'Hare Intl

Mon 6/9

8:15 am-9:20 am

Nonstop1h 05m

$179

MadisonChicago

MSN - ORD

MSNORD

Madison Truax Field

Thu 5/29

5:09 am-6:10 am

Nonstop1h 01m

Chicago O'Hare Intl

Thu 6/5

8:16 am-9:20 am

Nonstop1h 04m

$179

Eau ClaireChicago

EAU - ORD

EAUORD

Eau Claire

Sat 6/14

5:30 am-6:53 am

Nonstop1h 23m

Chicago O'Hare Intl

Sat 6/21

12:25 pm-1:54 pm

Nonstop1h 29m

$180

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

$181

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

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 May 1, 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 May 1, 2025.

The most flights from USWI to CHI are scheduled on a Wednesday (47 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (12 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 May 1, 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
9,972 reviews

Overall

8.0

Entertainment

7.1

Comfort

7.9

Boarding

8.1

Crew

8.5

Food

7.1

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
9,972 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Overall

8.0

Entertainment

7.1

Comfort

7.9

Boarding

8.1

Crew

8.5

Food

7.1

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
4,294 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Overall

8.0

Entertainment

7.1

Comfort

7.9

Boarding

8.1

Crew

8.5

Food

7.1

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
7,934 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Overall

8.0

Entertainment

7.1

Comfort

7.9

Boarding

8.1

Crew

8.5

Food

7.1

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
8,696 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Overall

8.0

Entertainment

7.1

Comfort

7.9

Boarding

8.1

Crew

8.5

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Allegiant Air
7.3
Good
734 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Overall

8.0

Entertainment

7.1

Comfort

7.9

Boarding

8.1

Crew

8.5

Food

7.1

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 $52 on Sun Country Air. Other airlines that offer cheap prices include Frontier from $89 and Southwest from $90 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 Midway. You may also consider Minneapolis St Paul - Chicago O'Hare Intl 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 $901, our data indicates the cheapest price to be $118. The most popular route (Minneapolis St Paul - Chicago Midway), is priced around $177.

  • 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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$179Average$280FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$179Average$319FlexibilityNo cancel feeOn-time71%
DeltaCheapest$198Average$208FlexibilityNo cancel feeOn-timeN/A

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