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Wisconsin Dells

$79+ Cheap flights from Chicago (CHI) to Wisconsin Dells, WI

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 9/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MSN
ago. 25 — sep. 11
lun. 8/25
lun. 9/1
1 adult, Economy
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Cheap flight deals from Chicago to Wisconsin Dells

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

Round-trip from

$179
(American Airlines)

One-way from

$79
(Frontier)

Popular in

April

Cheapest in

September

Average price

$276
From Chicago (CHI) to Wisconsin Dells
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One-way flight from Chicago (CHI) to Wisconsin Dells
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Highest demand for flights based on searches. 40% potential increase in price ($238 potential increase over avg. RT price).
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Cheapest flight prices on average. 12% potential price decrease ($41 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find flight deals from Chicago to Wisconsin Dells

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

This American Airlines deal was found by Cheapflights users on 8/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 9/98:55 pmORD - MSN
Nonstop1h 05mAmerican Airlines
mié. 9/172:54 pmMSN - ORD
Nonstop1h 11mAmerican Airlines
Deal found 8/18$179
This American Airlines deal was found by Cheapflights users on 8/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 9/118:47 amORD - MSN
Nonstop1h 12mAmerican Airlines
dom. 9/148:00 amMSN - ORD
Nonstop1h 09mAmerican Airlines
Deal found 8/18$181
This American Airlines deal was found by Cheapflights users on 8/20. 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.
dom. 9/78:27 amORD - MSN
Nonstop1h 07mAmerican Airlines
mié. 9/242:54 pmMSN - ORD
Nonstop1h 11mAmerican Airlines
Deal found 8/20$184
This American Airlines deal was found by Cheapflights users on 8/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 9/28:10 amORD - MSN
Nonstop1h 01mAmerican Airlines
sáb. 9/62:01 pmMSN - ORD
Nonstop1h 11mAmerican Airlines
Deal found 8/18$189
This American Airlines deal was found by Cheapflights users on 8/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/114:40 pmORD - MSN
Nonstop0h 53mAmerican Airlines
lun. 12/156:47 pmMSN - ORD
Nonstop1h 03mAmerican Airlines
Deal found 8/18$213
This American Airlines deal was found by Cheapflights users on 8/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/1010:23 amORD - MSN
Nonstop1h 02mAmerican Airlines
dom. 10/128:25 pmMSN - ORD
Nonstop1h 05mAmerican Airlines
Deal found 8/19$224
This American Airlines deal was found by Cheapflights users on 8/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 8/196:43 pmORD - MSN
Nonstop1h 14mAmerican Airlines
dom. 9/148:18 pmMSN - ORD
Nonstop1h 09mAmerican Airlines
Deal found 8/19$225
This United Airlines deal was found by Cheapflights users on 8/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 9/223:40 pmORD - MSN
Nonstop1h 04mUnited Airlines
dom. 9/285:20 amMSN - ORD
Nonstop1h 10mUnited Airlines
Deal found 8/18$239
This lol.travel deal was found by Cheapflights users on 8/19. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 9/22:02 pmORD - MSN
Nonstop1h 00mUnited Airlines
sáb. 9/62:31 pmMSN - ORD
Nonstop1h 11mUnited Airlines
Deal found 8/19$244
This United Airlines deal was found by Cheapflights users on 8/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/183:35 pmORD - MSN
Nonstop1h 10mUnited Airlines
lun. 12/298:15 amMSN - ORD
Nonstop1h 21mUnited Airlines
Deal found 8/18$254
This American Airlines deal was found by Cheapflights users on 8/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 8/226:31 pmORD - MSN
Nonstop1h 13mAmerican Airlines
lun. 8/258:14 pmMSN - ORD
Nonstop1h 05mAmerican Airlines
Deal found 8/19$259
This Delta deal was found by Cheapflights users on 8/18. 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. 8/191:08 pmMDW - MSN
1 stop7h 15mDelta
sáb. 8/239:25 amMSN - MDW
1 stop9h 12mDelta
Deal found 8/18$1,044

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Wisconsin Dells 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 agosto 20, 2025.
Use the filters below to find and compare flights from Chicago to Wisconsin Dells that are best for you.

Fly from

Chicago

Fly to

Wisconsin Dells

Route

Depart

Return

Price

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

mié. 9/17

8:38 am-9:43 am

Nonstop1h 05m

Madison Truax Field

mié. 9/24

2:54 pm-4:05 pm

Nonstop1h 11m

$179

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

jue. 9/11

8:45 am-9:45 am

Nonstop1h 00m

Madison Truax Field

dom. 9/14

3:58 pm-5:05 pm

Nonstop1h 07m

$179

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

mié. 10/1

8:38 am-9:43 am

Nonstop1h 05m

Madison Truax Field

vie. 10/31

8:25 am-9:30 am

Nonstop1h 05m

$179

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

dom. 9/28

8:47 am-9:59 am

Nonstop1h 12m

Madison Truax Field

dom. 10/5

8:18 pm-9:27 pm

Nonstop1h 09m

$179

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

mar. 9/9

8:55 pm-10:00 pm

Nonstop1h 05m

Madison Truax Field

mié. 9/17

2:54 pm-4:05 pm

Nonstop1h 11m

$179

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

jue. 9/11

8:47 am-9:59 am

Nonstop1h 12m

Madison Truax Field

dom. 9/14

8:18 pm-9:27 pm

Nonstop1h 09m

$179

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

mié. 9/24

1:23 pm-2:24 pm

Nonstop1h 01m

Madison Truax Field

sáb. 9/27

6:24 pm-7:40 pm

Nonstop1h 16m

$179

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

jue. 9/18

8:47 am-9:59 am

Nonstop1h 12m

Madison Truax Field

jue. 9/25

8:18 pm-9:27 pm

Nonstop1h 09m

$179

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

dom. 9/7

8:27 am-9:34 am

Nonstop1h 07m

Madison Truax Field

mié. 9/24

2:54 pm-4:05 pm

Nonstop1h 11m

$184

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

jue. 9/4

10:42 am-7:14 pm

1 stop8h 32m

$79

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/18

Showing 1-10 of 19 results
1
2

Best time to book a flight from Chicago to Wisconsin Dells

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

What is the cheapest time of day to fly from CHI to W1S?

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

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Wisconsin Dells as you normally would.

What is the cheapest day to fly from Chicago to Wisconsin Dells?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Wisconsin Dells. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago to Wisconsin Dells flight should consider departing on Friday evenings when fares are most often at their lowest. Sunday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago to Wisconsin Dells

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

The most flights from CHI to W1S are scheduled on a Monday (42 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (20 on average).

Reviews of airlines servicing Wisconsin Dells

Get insights into the airlines that provide service to Wisconsin Dells. 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 Dells. Reviews last updated agosto 20, 2025.
Get a feel of what it's like to fly with United Airlines from Chicago to Wisconsin Dells by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,928 reviews

Overall

7.4

Crew

8.1

Food

6.6

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
United Airlines
7.4
Good
8,928 reviews
United Airlines
7.4
Good
8,928 reviews

Overall

7.4

Crew

8.1

Food

6.6

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

Related info for your journey

Find useful and relevant information for your journey from Chicago to Wisconsin Dells. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago to Wisconsin Dells?

    Airlines like American Airlines fly from Chicago to Wisconsin Dells in about 1h 05m. The time it takes to get you to your destination is usually consistent. There are 108 mi between Chicago and Wisconsin Dells. Most flights are nonstop.

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

    No one likes to see their flight delayed. When booking a flight from Chicago to Wisconsin Dells consider choosing Republic Airways (86%), GoJet (77%) or United Airlines (74%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Chicago to Wisconsin Dells?

    The cheapest flight price from Chicago to Wisconsin Dells is $247. On average you can expect to pay $309. The most popular route, (Chicago O'Hare Intl - Madison Truax Field), can usually be booked for $179.

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

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

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

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

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

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

    Currently, January is the cheapest month in which you can book a flight from Chicago to Wisconsin Dells (average of $338). Flying from Chicago to Wisconsin Dells in March is currently the most expensive (average of $422). 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 Dells

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Chicago to Wisconsin Dells

Discover the top 3 airlines that operate flights from Chicago to Wisconsin Dells. 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 agosto 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Denver Air ConnectionCheapest$112Average$171FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$179Average$318FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$179Average$322FlexibilityNo cancel feeOn-time71%

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