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$69+ Cheap flights from Chicago (CHI) to Wisconsin

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 6/30. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MKE
feb. 25 — mar. 41
mar. 2/25
mar. 3/4
1 adult, Economy
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Cheap flight deals from Chicago to Wisconsin

Keep the following information in mind while searching for Chicago to Wisconsin flight deals. Data was last updated febrero 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$132
(Delta)

One-way from

$69
(Sun Country Air)

Popular in

December

Cheapest in

September

Average price

$249

Good round-trip deal

$180 or less

Good one-way deal

$98 or less
Provider with most accurate pricing for Chicago (CHI)-Milwaukee-Mitchell flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Milwaukee-Mitchell flights.
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From Chicago (CHI) to Wisconsin
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One-way flight from Chicago (CHI) to Wisconsin
Search Deals
Highest demand for flights based on searches. 18% potential increase in price ($68 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($23 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Wisconsin.
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Price to beat on a one-way flight from Chicago (CHI) to Wisconsin.
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Find flight deals from Chicago to Wisconsin

Cheapest flights from Chicago to Wisconsin
Explore the most affordable flight options available from Chicago to Wisconsin. Find the lowest fares from popular airlines and budget airlines, with prices last updated on febrero 20, 2025.

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.
vie. 3/712:15 pmORD - MSP
Nonstop1h 35mDelta
lun. 3/108:15 pmMSP - ORD
Nonstop1h 32mDelta
Deal found 2/20$132
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.
mié. 3/121:16 pmMDW - MSP
Nonstop1h 39mDelta
vie. 3/217:59 amMSP - MDW
Nonstop1h 46mDelta
Deal found 2/20$132
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.
lun. 3/318:33 pmORD - MSP
1 stop17h 45mSpirit Airlines
mié. 4/24:27 pmMSP - ORD
1 stop16h 17mSpirit Airlines
Deal found 2/20$135
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 6/68:10 pmORD - MSP
Nonstop1h 40mSun Country Air
dom. 6/85:30 pmMSP - ORD
Nonstop1h 41mSun Country Air
Deal found 2/19$136
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 4/38:10 amMDW - MSP
1 stop7h 10mSouthwest
lun. 4/75:45 pmMSP - MDW
1 stop4h 00mSouthwest
Deal found 2/19$137
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 4/36:30 pmORD - MSP
Nonstop1h 40mMultiple Airlines
sáb. 4/56:00 amMSP - ORD
1 stop7h 20mMultiple Airlines
Deal found 2/19$139
This Flightnetwork 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 4/176:45 amORD - MSP
1 stop16h 48mFrontier
lun. 4/216:00 amMSP - ORD
1 stop18h 37mFrontier
Deal found 2/20$152
This Booking.com 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 4/176:45 amMDW - MSP
1 stop16h 48mFrontier
lun. 4/216:00 amMSP - MDW
1 stop18h 21mFrontier
Deal found 2/19$160
This Delta deal was found by Cheapflights users on 2/18. 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.
sáb. 3/227:10 pmORD - DLH
1 stop3h 47mDelta
mar. 3/256:05 pmDLH - ORD
1 stop3h 42mDelta
Deal found 2/18$178
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 4/1810:55 amORD - EAU
Nonstop1h 25mUnited Airlines
dom. 4/205:35 amEAU - ORD
Nonstop1h 27mUnited Airlines
Deal found 2/19$180
This Delta deal was found by Cheapflights users on 2/18. 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.
mar. 3/410:19 amMDW - DLH
1 stop3h 30mDelta
mar. 3/112:34 pmDLH - MDW
1 stop3h 44mDelta
Deal found 2/18$183
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 5/18:45 amORD - MSP
Nonstop1h 33mUnited Airlines
sáb. 5/310:00 amMSP - ORD
Nonstop1h 37mUnited Airlines
Deal found 2/19$193

Find flights from Chicago to Wisconsin within your budget

Customize your flight search to find flights from Chicago to Wisconsin 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 febrero 20, 2025.

Fly from

Chicago

Fly to

Wisconsin

Route

Depart

Return

Price

ChicagoMinneapolis

ORD - MSP

ORDMSP

Chicago O'Hare Intl

vie. 3/7

12:15 pm-1:50 pm

Nonstop1h 35m

Minneapolis St Paul

lun. 3/10

8:15 pm-9:47 pm

Nonstop1h 32m

$132

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

mié. 3/12

1:16 pm-2:55 pm

Nonstop1h 39m

Minneapolis St Paul

vie. 3/21

7:59 am-9:45 am

Nonstop1h 46m

$132

ChicagoMinneapolis

ORD - MSP

ORDMSP

Chicago O'Hare Intl

lun. 3/31

8:33 pm-2:18 pm

1 stop17h 45m

Minneapolis St Paul

mié. 4/2

4:27 pm-8:44 am

1 stop16h 17m

$135

ChicagoMinneapolis

ORD - MSP

ORDMSP

Chicago O'Hare Intl

vie. 6/6

8:10 pm-9:50 pm

Nonstop1h 40m

Minneapolis St Paul

dom. 6/8

5:30 pm-7:11 pm

Nonstop1h 41m

$136

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

jue. 4/3

8:10 am-3:20 pm

1 stop7h 10m

Minneapolis St Paul

lun. 4/7

5:45 pm-9:45 pm

1 stop4h 00m

$137

ChicagoMinneapolis

ORD - MSP

ORDMSP

Chicago O'Hare Intl

jue. 4/3

6:30 pm-8:10 pm

Nonstop1h 40m

Minneapolis St Paul

sáb. 4/5

6:00 am-1:20 pm

1 stop7h 20m

$139

ChicagoMinneapolis

ORD - MSP

ORDMSP

Chicago O'Hare Intl

jue. 4/17

6:45 am-11:33 pm

1 stop16h 48m

Minneapolis St Paul

lun. 4/21

6:00 am-12:37 am

1 stop18h 37m

$152

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

jue. 4/17

6:45 am-11:33 pm

1 stop16h 48m

Minneapolis St Paul

lun. 4/21

6:00 am-12:21 am

1 stop18h 21m

$160

ChicagoDuluth

ORD - DLH

ORDDLH

Chicago O'Hare Intl

sáb. 3/22

7:10 pm-10:57 pm

1 stop3h 47m

Duluth Intl

mar. 3/25

6:05 pm-9:47 pm

1 stop3h 42m

$178

ChicagoEau Claire

ORD - EAU

ORDEAU

Chicago O'Hare Intl

vie. 4/18

10:55 am-12:20 pm

Nonstop1h 25m

Eau Claire

dom. 4/20

5:35 am-7:02 am

Nonstop1h 27m

$180

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 Chicago to Wisconsin

Have a flexible travel schedule? Discover the best time to fly to Wisconsin from Chicago 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 Chicago to Wisconsin

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

What is the cheapest month to book a flight from Chicago to Wisconsin?

Currently, February is the cheapest month in which you can book a flight from Chicago to Wisconsin (average of $280). Flying from Chicago to Wisconsin in June is currently the most expensive (average of $376). 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 CHI to WI?

Find hourly flight availability from Chicago to Wisconsin. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated febrero 20, 2025.

When flying from Chicago to Wisconsin, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Chicago to Wisconsin

Explore weekly flight availability from Chicago to Wisconsin. 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 febrero 20, 2025.

The most flights from CHI to USWI are scheduled on a Tuesday (44 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (37 on average).

Rainfall in Wisconsin by month

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

In terms of precipitation, rainfall in Wisconsin ranges from 1.4 - 4.0 inches per month. June is typically the wettest month, when rainfall can reach 4.0 in. January is typically the driest time to visit Wisconsin when rainfall is around 1.4 in.

Temperature in Wisconsin by month

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

If weather is an important factor for your trip to Wisconsin, 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 21.2 F).

Reviews of airlines servicing Wisconsin

Get insights into the airlines that provide service to Wisconsin. 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 Wisconsin. Reviews last updated febrero 20, 2025.
See what other customers who have flown with Southwest, Delta and United Airlines from Chicago to Wisconsin have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.1

Boarding

8.2

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

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.1

Boarding

8.2

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

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.1

Boarding

8.2

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

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.1

Boarding

8.2

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.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.1

Boarding

8.2

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.

Sun Country Air
7.0
Good
374 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.1

Boarding

8.2

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 Chicago to Wisconsin. 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 Chicago to Wisconsin one-way?

    $69 is the cheapest one-way deal found within the past few days, from Sun Country Air. You may also be able to find cheap deals on Southwest and Frontier, with prices starting from $69 and $71, respectively.

  • What are the most popular routes from Chicago to Wisconsin?

    Most travelers choose Chicago O'Hare Intl - Minneapolis St Paul, Chicago Midway - Minneapolis St Paul or Chicago O'Hare Intl - Duluth Intl when deciding on the best route from Chicago to Wisconsin.

  • What are the most reliable airlines from Chicago to Wisconsin?

    Before booking your flight to Wisconsin from Chicago, check out the most reliable airlines to get you to your destination on time: Republic Airways (96%), Qatar Airways (81%), Alaska Airlines( 77%).

  • What are the cheapest flights from Chicago to Wisconsin?

    On average you can expect to pay $221 for a flight from Chicago to Wisconsin. The cheapest flight overall is $94 while the most popular route, (Chicago O'Hare Intl - Minneapolis St Paul) is currently priced at $116.

  • Can I find deals for flights from Chicago to Wisconsin that include hotel bookings?

    Yes. In addition to deals on Chicago to Wisconsin flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Wisconsin?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Wisconsin.

  • Can I find deals for business class flights from Chicago to Wisconsin?

    Yes. Cheapflights offers flight deals from Chicago to Wisconsin 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 Chicago to Wisconsin?

    Currently, February is the cheapest month in which you can book a flight from Chicago to Wisconsin (average of $280). Flying from Chicago to Wisconsin in June is currently the most expensive (average of $376). 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.

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Alternative routes for Chicago to Wisconsin

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Chicago to Wisconsin

Discover the top 2 airlines that operate flights from Chicago to Wisconsin. 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 febrero 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$179Average$311FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$184Average$374FlexibilityNo cancel feeOn-time71%
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