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Wisconsin Dells

$124+ 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 11/23. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MSN
Nov 28 — Dec 51
Fri 11/28
Fri 12/5
1 adult, Economy
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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 October 29, 2025.

This American Airlines deal was found by Cheapflights users on 10/27. 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.
Mon 11/2411:40 amORD - MSN
Nonstop1h 04mAmerican Airlines
Mon 12/18:12 pmMSN - ORD
Nonstop1h 18mAmerican Airlines
Deal found 10/27$179
This American Airlines deal was found by Cheapflights users on 10/27. 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 11/208:22 amORD - MSN
Nonstop1h 02mAmerican Airlines
Sun 11/231:19 pmMSN - ORD
Nonstop1h 13mAmerican Airlines
Deal found 10/27$180
This American Airlines deal was found by Cheapflights users on 10/27. 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 11/168:15 amORD - MSN
Nonstop1h 03mAmerican Airlines
Sun 11/231:19 pmMSN - ORD
Nonstop1h 13mAmerican Airlines
Deal found 10/27$184
This United Airlines deal was found by Cheapflights users on 10/27. 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.
Tue 11/1110:35 amORD - MSN
Nonstop1h 10mUnited Airlines
Sat 11/153:58 pmMSN - ORD
Nonstop1h 11mUnited Airlines
Deal found 10/27$189
This American Airlines deal was found by Cheapflights users on 10/28. 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 11/169:43 pmORD - MSN
Nonstop1h 06mAmerican Airlines
Mon 11/245:00 amMSN - ORD
Nonstop1h 15mAmerican Airlines
Deal found 10/28$194
This United Airlines deal was found by Cheapflights users on 10/28. 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.
Mon 12/223:35 pmORD - MSN
Nonstop1h 10mUnited Airlines
Sun 12/2810:45 amMSN - ORD
Nonstop1h 20mUnited Airlines
Deal found 10/28$203
This United Airlines deal was found by Cheapflights users on 10/27. 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.
Tue 11/44:50 pmORD - MSN
Nonstop1h 00mUnited Airlines
Sat 11/156:20 amMSN - ORD
Nonstop1h 11mUnited Airlines
Deal found 10/27$204
This American Airlines deal was found by Cheapflights users on 10/26. 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 10/311:17 pmORD - MSN
Nonstop1h 02mAmerican Airlines
Sun 11/25:00 amMSN - ORD
Nonstop1h 15mAmerican Airlines
Deal found 10/26$228
This American Airlines deal was found by Cheapflights users on 10/27. 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 12/128:15 amORD - MSN
Nonstop1h 04mAmerican Airlines
Fri 12/198:10 pmMSN - ORD
Nonstop1h 20mAmerican Airlines
Deal found 10/27$232
This American Airlines deal was found by Cheapflights users on 10/27. 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.
Mon 11/38:15 amORD - MSN
Nonstop1h 03mAmerican Airlines
Fri 12/198:10 pmMSN - ORD
Nonstop1h 20mAmerican Airlines
Deal found 10/27$251
This American Airlines deal was found by Cheapflights users on 10/28. 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 10/298:50 amORD - MSN
Nonstop1h 16mAmerican Airlines
Wed 11/51:53 pmMSN - ORD
Nonstop1h 13mAmerican Airlines
Deal found 10/28$270
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/116:26 pmMDW - MSN
2 stops23h 02mMultiple Airlines
Sat 11/156:08 pmMSN - MDW
1 stop15h 04mMultiple Airlines
Deal found 10/27$321

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 October 29, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$179
(American Airlines)

One-way from

$124
(United Airlines)

Popular in

April

Cheapest in

December

Average price

$315
Provider with most accurate pricing for Chicago (CHI)-Madison Truax Field flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Madison Truax Field flights.
Search Deals
From Chicago (CHI) to Wisconsin Dells
Search Deals
One-way flight from Chicago (CHI) to Wisconsin Dells
Search Deals
Highest demand for flights based on searches. 36% potential increase in price ($217 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 11% potential price decrease ($40 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

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 October 29, 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

Mon 11/24

11:40 am-12:44 pm

Nonstop1h 04m

Madison Truax Field

Mon 12/1

8:12 pm-9:30 pm

Nonstop1h 18m

$179

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Thu 11/20

8:22 am-9:24 am

Nonstop1h 02m

Madison Truax Field

Sun 11/23

1:19 pm-2:32 pm

Nonstop1h 13m

$180

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Sun 11/16

8:15 am-9:18 am

Nonstop1h 03m

Madison Truax Field

Sun 11/23

1:19 pm-2:32 pm

Nonstop1h 13m

$184

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Tue 11/11

10:35 am-11:45 am

Nonstop1h 10m

Madison Truax Field

Sat 11/15

3:58 pm-5:09 pm

Nonstop1h 11m

$189

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Tue 11/11

7:12 pm-8:19 pm

Nonstop1h 07m

Madison Truax Field

Sat 11/15

9:48 am-11:02 am

Nonstop1h 14m

$189

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Tue 11/11

8:14 am-9:17 am

Nonstop1h 03m

Madison Truax Field

Sun 11/16

7:00 am-8:16 am

Nonstop1h 16m

$189

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Fri 4/24

7:50 pm-8:54 pm

Nonstop1h 04m

Madison Truax Field

Sun 4/26

7:00 am-8:05 am

Nonstop1h 05m

$203

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Fri 12/12

8:15 am-9:19 am

Nonstop1h 04m

Madison Truax Field

Fri 12/19

8:10 pm-9:30 pm

Nonstop1h 20m

$232

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Sat 3/14

2:00 pm-3:02 pm

Nonstop1h 02m

Madison Truax Field

Tue 3/17

6:30 am-7:42 am

Nonstop1h 12m

$239

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Tue 11/11

6:26 pm-5:28 pm

2 stops23h 02m

Madison Truax Field

Sat 11/15

6:08 pm-9:12 am

1 stop15h 04m

$321

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/26

Showing 1-10 of 32 results
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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 October 29, 2025.

A simple way to save on the total cost of your ticket is to fly from Chicago to Wisconsin Dells in the afternoon. If you’re flexible enough to do this you can expect to save up to 30% on your trip compared to booking a flight in the evening.

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 Thursday at noon when fares are most often at their lowest. Wednesday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

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 October 29, 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
8,999 reviews

Overall

7.4

Comfort

7.3

Entertainment

7.1

Food

6.6

Boarding

7.7

Crew

8.1

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
United Airlines
7.4
Good
8,999 reviews
United Airlines
7.4
Good
8,999 reviews

Overall

7.4

Comfort

7.3

Entertainment

7.1

Food

6.6

Boarding

7.7

Crew

8.1

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000

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 and United Airlines fly from Chicago to Wisconsin Dells in about 1h 04m. 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 GoJet (85%), ANA (81%) or Envoy Air (81%) 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 $279. On average you can expect to pay $308. The most popular route, (Chicago O'Hare Intl - Madison Truax Field), can usually be booked for $189.

  • 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.

See more FAQs

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Alternative routes for Chicago to Wisconsin Dells

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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 October 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
Denver Air ConnectionCheapest$130Average$172FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$179Average$331FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$199Average$323FlexibilityNo cancel feeOn-time69%

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