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Wisconsin Dells

$157+ 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 5/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MSN
Apr 20 — Apr 271
Mon 4/20
Mon 4/27
1 adult, Economy
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Cheap 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 March 21, 2026.

This United Airlines deal was found by Cheapflights users on 3/16. 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.
Wed 4/157:45 am
ORD
-
MSN
Nonstop1h 11m
United Airlines
Wed 4/222:44 pm
MSN
-
ORD
Nonstop1h 12m
United Airlines
Deal found 3/16$239
This American Airlines deal was found by Cheapflights users on 3/18. 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.
Thu 4/97:39 am
ORD
-
MSN
Nonstop1h 06m
American Airlines
Sun 4/125:30 am
MSN
-
ORD
Nonstop1h 17m
American Airlines
Deal found 3/18$241
This American Airlines deal was found by Cheapflights users on 3/16. 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 5/112:36 pm
ORD
-
MSN
Nonstop1h 12m
American Airlines
Fri 5/88:24 pm
MSN
-
ORD
Nonstop1h 16m
American Airlines
Deal found 3/16$242
This American Airlines deal was found by Cheapflights users on 3/16. 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 3/318:02 am
ORD
-
MSN
Nonstop1h 06m
American Airlines
Sat 4/43:03 pm
MSN
-
ORD
Nonstop1h 07m
American Airlines
Deal found 3/16$249
This American Airlines deal was found by Cheapflights users on 3/17. 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 3/317:44 pm
ORD
-
MSN
Nonstop1h 05m
American Airlines
Tue 4/79:18 am
MSN
-
ORD
Nonstop1h 13m
American Airlines
Deal found 3/17$254
This American Airlines deal was found by Cheapflights users on 3/16. 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 3/266:30 pm
ORD
-
MSN
Nonstop1h 06m
American Airlines
Mon 3/306:15 am
MSN
-
ORD
Nonstop1h 14m
American Airlines
Deal found 3/16$264
This United Airlines deal was found by Cheapflights users on 3/18. 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.
Wed 4/17:45 am
ORD
-
MSN
Nonstop1h 11m
United Airlines
Sat 4/48:30 am
MSN
-
ORD
Nonstop1h 07m
United Airlines
Deal found 3/18$269
This United Airlines deal was found by Cheapflights users on 3/17. 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.
Thu 3/269:35 pm
ORD
-
MSN
Nonstop0h 57m
United Airlines
Sat 3/286:30 am
MSN
-
ORD
Nonstop1h 12m
United Airlines
Deal found 3/17$299
This United Airlines deal was found by Cheapflights users on 3/18. 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.
Thu 4/99:00 am
ORD
-
MSN
Nonstop1h 11m
United Airlines
Sun 4/128:30 am
MSN
-
ORD
Nonstop1h 07m
United Airlines
Deal found 3/18$301
This United Airlines deal was found by Cheapflights users on 3/19. 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.
Tue 5/58:13 pm
ORD
-
MSN
Nonstop1h 07m
United Airlines
Sat 5/92:25 pm
MSN
-
ORD
Nonstop1h 11m
United Airlines
Deal found 3/19$309
This Kiwi.com deal was found by Cheapflights users on 3/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/189:14 am
MDW
-
MSN
1 stop8h 42m
Multiple Airlines
Sat 4/256:36 pm
MSN
-
MDW
1 stop26h 16m
Multiple Airlines
Deal found 3/20$403
This Kiwi.com deal was found by Cheapflights users on 3/16. 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.
Wed 4/156:30 am
MDW
-
MSN
2 stops11h 26m
Multiple Airlines
Wed 4/226:36 pm
MSN
-
MDW
1 stop12h 50m
Multiple Airlines
Deal found 3/16$471

Find 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 March 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$239
(United Airlines)

One-way from

$157
(Kiwi.com)

Popular in

April

Cheapest in

December

Average price

$449
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. 28% potential increase in price ($152 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($25 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
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 March 21, 2026.
Use the filters below to find and compare flights from Chicago to Wisconsin Dells that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Thu 4/30

9:50 pm-10:54 pm

Nonstop1h 04m

Madison Truax Field

Sun 5/3

2:30 pm-3:42 pm

Nonstop1h 12m

$239
Quickest round-trip

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Wed 4/15

8:15 pm-9:21 pm

Nonstop1h 06m

Madison Truax Field

Wed 4/22

8:30 am-9:37 am

Nonstop1h 07m

$239

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Thu 4/9

9:00 am-10:11 am

Nonstop1h 11m

Madison Truax Field

Sun 4/12

10:05 am-11:15 am

Nonstop1h 10m

$239

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Wed 4/1

7:45 am-8:56 am

Nonstop1h 11m

Madison Truax Field

Sat 4/4

8:30 am-9:37 am

Nonstop1h 07m

$269

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Tue 4/21

8:15 pm-9:21 pm

Nonstop1h 06m

Madison Truax Field

Sat 4/25

5:55 pm-7:05 pm

Nonstop1h 10m

$299

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Fri 3/27

7:45 pm-8:55 pm

Nonstop1h 10m

Madison Truax Field

Sun 3/29

6:30 am-7:42 am

Nonstop1h 12m

$299

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Tue 5/5

8:13 pm-9:20 pm

Nonstop1h 07m

Madison Truax Field

Sat 5/9

2:25 pm-3:36 pm

Nonstop1h 11m

$309

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Fri 4/3

8:15 pm-9:21 pm

Nonstop1h 06m

Madison Truax Field

Tue 4/7

2:44 pm-3:56 pm

Nonstop1h 12m

$339

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

Sat 4/18

8:00 am-5:56 pm

1 stop9h 56m

Madison Truax Field

Sat 4/25

9:48 am-6:20 pm

1 stop8h 32m

$359

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Sat 4/18

9:14 am-5:56 pm

1 stop8h 42m

Madison Truax Field

Sat 4/25

6:36 pm-8:52 pm

1 stop26h 16m

$403

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/16

Showing 1-10 of 28 resultsSorted by cheapest first
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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 March 21, 2026.

A simple way to save on the total cost of your ticket is to fly from Chicago to Wisconsin Dells at noon. If you’re flexible enough to do this you can expect to save up to 16% on your trip compared to booking a flight in the afternoon.

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 March 14, 2026.

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.

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 March 21, 2026.

The most flights from CHI to W1S are scheduled on a Monday (43 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (18 on average).

How much does it cost to fly round-trip from Chicago to Wisconsin Dells?

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 March 21, 2026.
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
9,452 reviews

Crew

8.1

Food

6.6

Boarding

7.7

Overall

7.4

Entertainment

7.1

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
United Airlines
7.4
Good
9,452 reviews
United Airlines
7.4
Good
9,452 reviews

Crew

8.1

Food

6.6

Boarding

7.7

Overall

7.4

Entertainment

7.1

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family

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 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 Envoy Air (67%), GoJet (65%) or Air New Zealand (64%) 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 $133. On average you can expect to pay $369. The most popular route, (Chicago O'Hare Intl - Madison Truax Field), can usually be booked for $239.

  • 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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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 March 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
Denver Air ConnectionCheapest$112Average$178FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$179Average$288FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$193Average$450FlexibilityNo cancel feeOn-time69%

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