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$58+ 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 6/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MKE
may. 6 — may. 131
mar. 5/6
mar. 5/13
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 mayo 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$106
(eDestinos)

One-way from

$58
(Cheapflightsfares)

Popular in

December

Cheapest in

April

Average price

$228

Good round-trip deal

$184 or less

Good one-way deal

$128 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
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Highest demand for flights based on searches. 27% potential increase in price ($104 potential increase over avg. RT price).
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Cheapest flight prices on average. 11% potential price decrease ($29 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 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 mayo 1, 2025.

This eDestinos 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 6/17:00 amORD - MSP
Nonstop1h 44mSun Country Air
jue. 6/53:36 pmMSP - ORD
Nonstop1h 39mSun Country Air
Deal found 4/30$106
This FlightHub deal was found by Cheapflights users on 5/1. 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. 5/158:05 pmORD - MSP
Nonstop1h 44mMultiple Airlines
lun. 5/196:00 amMSP - ORD
1 stop17h 41mMultiple Airlines
Deal found 5/1$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.
lun. 6/98:20 amORD - GRB
Nonstop1h 03mAmerican Airlines
mar. 7/86:19 pmGRB - ORD
Nonstop1h 14mAmerican Airlines
Deal found 4/30$179
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 5/277:55 pmORD - MKE
Nonstop1h 05mUnited Airlines
mar. 6/38:35 amMKE - ORD
Nonstop1h 05mUnited Airlines
Deal found 4/29$179
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.
jue. 5/2210:24 pmORD - ATW
Nonstop1h 10mAmerican Airlines
dom. 5/254:37 pmATW - ORD
Nonstop1h 13mAmerican Airlines
Deal found 4/29$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.
jue. 5/296:24 amORD - MSP
Nonstop1h 30mDelta
sáb. 5/317:05 amMSP - ORD
Nonstop1h 29mDelta
Deal found 4/30$179
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.
mar. 6/37:00 amORD - MSN
Nonstop1h 01mAmerican Airlines
sáb. 6/76:39 pmMSN - ORD
Nonstop1h 10mAmerican Airlines
Deal found 4/29$179
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.
sáb. 5/249:20 amMDW - MSP
Nonstop1h 39mDelta
dom. 5/254:15 pmMSP - MDW
Nonstop1h 30mDelta
Deal found 4/29$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.
vie. 6/1310:25 pmORD - MKE
Nonstop0h 55mAmerican Airlines
vie. 6/201:06 pmMKE - ORD
Nonstop1h 02mAmerican Airlines
Deal found 4/30$180
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.
sáb. 6/149:07 pmORD - EAU
Nonstop1h 23mUnited Airlines
sáb. 6/215:30 amEAU - ORD
Nonstop1h 23mUnited Airlines
Deal found 4/30$180
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.
sáb. 6/145:01 amORD - MSP
1 stop10h 00mFrontier
sáb. 6/214:13 pmMSP - ORD
1 stop8h 01mFrontier
Deal found 4/30$182
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.
sáb. 6/146:20 amMDW - MSP
1 stop8h 41mFrontier
sáb. 6/214:13 pmMSP - MDW
1 stop6h 15mFrontier
Deal found 4/30$182

Cheapflights Fare Finder

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 mayo 1, 2025.
Use the filters below to find and compare flights from Chicago to Wisconsin that are best for you.

Fly from

Chicago

Fly to

Wisconsin

Route

Depart

Return

Price

ChicagoMinneapolis

ORD - MSP

ORDMSP

Chicago O'Hare Intl

dom. 6/1

7:00 am-8:44 am

Nonstop1h 44m

Minneapolis St Paul

jue. 6/5

3:36 pm-5:15 pm

Nonstop1h 39m

$106

ChicagoMinneapolis

ORD - MSP

ORDMSP

Chicago O'Hare Intl

jue. 5/29

10:00 am-7:55 pm

1 stop9h 55m

Minneapolis St Paul

jue. 6/5

3:36 pm-5:15 pm

Nonstop1h 39m

$158

ChicagoGreen Bay

ORD - GRB

ORDGRB

Chicago O'Hare Intl

lun. 6/9

8:20 am-9:23 am

Nonstop1h 03m

Green Bay Austin-Straubel

mar. 7/8

6:19 pm-7:33 pm

Nonstop1h 14m

$179

ChicagoMilwaukee

ORD - MKE

ORDMKE

Chicago O'Hare Intl

mar. 5/27

7:55 pm-9:00 pm

Nonstop1h 05m

Milwaukee-Mitchell

mar. 6/3

8:35 am-9:40 am

Nonstop1h 05m

$179

ChicagoMinneapolis

ORD - MSP

ORDMSP

Chicago O'Hare Intl

jue. 5/29

6:24 am-7:54 am

Nonstop1h 30m

Minneapolis St Paul

sáb. 5/31

7:05 am-8:34 am

Nonstop1h 29m

$179

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

jue. 5/22

10:24 pm-11:34 pm

Nonstop1h 10m

Appleton Intl

dom. 5/25

4:37 pm-5:50 pm

Nonstop1h 13m

$179

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

sáb. 5/24

9:20 am-10:59 am

Nonstop1h 39m

Minneapolis St Paul

dom. 5/25

4:15 pm-5:45 pm

Nonstop1h 30m

$179

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

mar. 6/3

7:00 am-8:01 am

Nonstop1h 01m

Madison Truax Field

sáb. 6/7

6:39 pm-7:49 pm

Nonstop1h 10m

$179

ChicagoEau Claire

ORD - EAU

ORDEAU

Chicago O'Hare Intl

sáb. 6/14

9:07 pm-10:30 pm

Nonstop1h 23m

Eau Claire

sáb. 6/21

5:30 am-6:53 am

Nonstop1h 23m

$180

ChicagoMilwaukee

ORD - MKE

ORDMKE

Chicago O'Hare Intl

vie. 6/13

10:25 pm-11:20 pm

Nonstop0h 55m

Milwaukee-Mitchell

vie. 6/20

2:50 pm-3:51 pm

Nonstop1h 01m

$180

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 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.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Wisconsin

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 mayo 1, 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 mayo 1, 2025.

The most flights from CHI to USWI are scheduled on a Wednesday (46 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 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 mayo 1, 2025.
See what other customers who have flown with Alaska Airlines, Southwest and Delta 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.
Alaska Airlines
8.0
Very good
9,968 reviews

Food

7.1

Comfort

7.9

Crew

8.5

Entertainment

7.1

Overall

8.0

Boarding

8.2

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
9,968 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Food

7.1

Comfort

7.9

Crew

8.5

Entertainment

7.1

Overall

8.0

Boarding

8.2

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
9,968 reviews

Food

7.1

Comfort

7.9

Crew

8.5

Entertainment

7.1

Overall

8.0

Boarding

8.2

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
9,968 reviews

Food

7.1

Comfort

7.9

Crew

8.5

Entertainment

7.1

Overall

8.0

Boarding

8.2

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
9,968 reviews

Food

7.1

Comfort

7.9

Crew

8.5

Entertainment

7.1

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
JetBlue
7.3
Good
2,924 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Food

7.1

Comfort

7.9

Crew

8.5

Entertainment

7.1

Overall

8.0

Boarding

8.2

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 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?

    $58 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 Delta and Frontier, with prices starting from $90 and $91, 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 (100%), Aer Lingus (78%), SkyWest Airlines( 72%).

  • What are the cheapest flights from Chicago to Wisconsin?

    On average you can expect to pay $272 for a flight from Chicago to Wisconsin. The cheapest flight overall is $184 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.

See more FAQs

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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 mayo 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$179Average$317FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$184Average$364FlexibilityNo cancel feeOn-time71%

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