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Wisconsin Dells

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

CHI — MSN
Nov 12 — Nov 191
Thu 11/12
Thu 11/19
1 adult, Economy
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Find flight deals from Chicago to Wisconsin Dells

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

June

Cheapest in

December

Average price

$289
Provider with most accurate pricing for Chicago (CHI)-Madison Truax Field flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Madison Truax Field flights.
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Highest demand for flights based on searches. 15% potential increase in price ($86 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($18 potential savings vs. average RT price).
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Average for round-trip flights in October 2026
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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?

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 26% on your trip compared to booking a flight at noon.

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

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. Sunday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Wisconsin Dells

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
10,350 reviews

Comfort

7.3

Entertainment

7.1

Overall

7.4

Boarding

7.7

Crew

8.1

Food

6.7

Reviews

1 / 20
2.0
Mediocre

Dawn,Aug 2026

ORD - DEN

I missed my connecting flight because our plane took off ten minutes late and then when we got to the airport another plane was in our shoot waiting to get fueled up and that took 30 minutes so I missed my connecting flight. I asked if I could get off and they assured me the plane would most likely wait for me since they know what time the planes get in because of an app. I was not happy. I had to wait till 7:25 to board the next flight and then that was delayed. Gates changed till 9:20. Terrible
United Airlines
7.4
Good
10,350 reviews
United Airlines
7.4
Good
10,350 reviews

Comfort

7.3

Entertainment

7.1

Overall

7.4

Boarding

7.7

Crew

8.1

Food

6.7

Reviews

1 / 20
2.0
Mediocre

Dawn,Aug 2026

ORD - DEN

I missed my connecting flight because our plane took off ten minutes late and then when we got to the airport another plane was in our shoot waiting to get fueled up and that took 30 minutes so I missed my connecting flight. I asked if I could get off and they assured me the plane would most likely wait for me since they know what time the planes get in because of an app. I was not happy. I had to wait till 7:25 to board the next flight and then that was delayed. Gates changed till 9:20. Terrible

Related info for your journey

  • 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 (84%), American Airlines (81%) or British Airways (80%) 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 $258. On average you can expect to pay $471. The most popular route, (Chicago O'Hare Intl - Madison Truax Field), can usually be booked for $289.

  • 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

Browse thousands of different options on Cheapflights for your next trip

Top 2 airlines flying from Chicago to Wisconsin Dells

AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$205Average$497FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$268Average$411FlexibilityNo cancel feeOn-time71%

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