Wisconsin Dells

$131+ 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 8/25. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MSN
jul. 8 — jul. 151
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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 julio 3, 2025.

Round-trip from

$179
(United Airlines)

One-way from

$131
(Orbitz)

Popular in

April

Cheapest in

December

Average price

$264
From Chicago (CHI) to Wisconsin Dells
One-way flight from Chicago (CHI) to Wisconsin Dells
Highest demand for flights based on searches. 37% potential increase in price ($223 potential increase over avg. RT price).
Cheapest flight prices on average. 13% potential price decrease ($44 potential savings vs. average RT price).
Average for round-trip flights in July 2025

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 julio 3, 2025.

This United Airlines deal was found by Cheapflights users on 7/2. 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.
mié. 8/2010:35 amORD - MSN
Nonstop1h 09mUnited Airlines
dom. 8/246:30 amMSN - ORD
Nonstop1h 07mUnited Airlines
Deal found 7/2$179
This American Airlines deal was found by Cheapflights users on 7/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 7/249:03 amORD - MSN
Nonstop1h 12mAmerican Airlines
dom. 7/278:27 pmMSN - ORD
Nonstop1h 03mAmerican Airlines
Deal found 7/1$180
This Mytrip deal was found by Cheapflights users on 7/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 8/167:05 amORD - MSN
1 stop10h 40mMultiple Airlines
sáb. 8/236:25 pmMSN - ORD
1 stop16h 01mMultiple Airlines
Deal found 7/2$509
This Delta deal was found by Cheapflights users on 7/2. 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. 7/186:20 pmMDW - MSN
1 stop14h 27mDelta
lun. 7/217:00 amMSN - MDW
1 stop11h 40mDelta
Deal found 7/2$815

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 julio 3, 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. 8/20

10:35 am-11:44 am

Nonstop1h 09m

Madison Truax Field

dom. 8/24

6:30 am-7:37 am

Nonstop1h 07m

$179

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

jue. 7/24

9:03 am-10:15 am

Nonstop1h 12m

Madison Truax Field

dom. 7/27

8:27 pm-9:30 pm

Nonstop1h 03m

$180

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

sáb. 8/16

7:05 am-5:45 pm

1 stop10h 40m

Madison Truax Field

sáb. 8/23

6:25 pm-10:26 am

1 stop16h 01m

$509

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

jue. 7/24

5:40 am-6:33 pm

1 stop12h 53m

Madison Truax Field

dom. 7/27

7:18 pm-9:41 am

1 stop14h 23m

$733

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

vie. 7/18

6:20 pm-8:47 am

1 stop14h 27m

Madison Truax Field

lun. 7/21

7:00 am-6:40 pm

1 stop11h 40m

$815

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

lun. 8/25

11:44 am-6:04 pm

1 stop6h 20m

$131

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

lun. 9/1

5:12 pm-6:14 pm

Nonstop1h 02m

$192

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

vie. 8/1

4:36 pm-9:39 am

1 stop17h 03m

$230

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

vie. 8/1

1:11 pm-9:39 am

2 stops20h 28m

$249

ChicagoMadison

ORD - MSN

ORDMSN

Chicago O'Hare Intl

lun. 7/7

12:45 pm-1:54 pm

Nonstop1h 09m

$310

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/1

Showing 1-10 of 11 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 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.

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 julio 3, 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 julio 3, 2025.

The most flights from CHI to W1S are scheduled on a Thursday (41 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (5 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 julio 3, 2025.
Get a feel of what it's like to fly with Delta, United Airlines, and American 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.
8.0
Very good

Crew

8.5

Food

7.3

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
8.0
Very good
8.0
Very good

Crew

8.5

Food

7.3

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
8.0
Very good

Crew

8.5

Food

7.3

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
8.0
Very good

Crew

8.5

Food

7.3

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
8.0
Very good

Crew

8.5

Food

7.3

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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.
  • What are the cheapest airlines to fly from Chicago to Wisconsin Dells one-way?

    $131 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on American Airlines and United Airlines, with prices starting from $192 and $310, respectively.

  • 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 Piedmont Airlines (96%), Republic Airways (89%) or ANA (86%) 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 $179. On average you can expect to pay $408. 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.

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 julio 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
Denver Air ConnectionCheapest$112Average$171FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$179Average$319FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$191Average$332FlexibilityNo cancel feeOn-time71%

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