$131 Find Cheap Flights from Chicago to Wisconsin Dells

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Wisconsin Dells departing on 9/5. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

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Cheap Flights from Chicago to Wisconsin Dells (CHI-MSN)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Wisconsin Dells that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Wisconsin Dells

Thu, Aug 21 - Thu, Aug 28
United Airlines Logo
12:45 pm - 1:45 pmORD-MSN
1h 00mnonstop
United Airlines Logo
6:30 am - 7:37 amMSN-ORD
1h 07mnonstop
$179United Airlines
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Sat, Aug 23 - Sat, Aug 30
American Airlines Logo
2:14 pm - 3:19 pmORD-MSN
1h 05mnonstop
American Airlines Logo
1:29 pm - 2:35 pmMSN-ORD
1h 06mnonstop
$180American Airlines
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Thu, Aug 7 - Thu, Aug 14
United Airlines Logo
2:00 pm - 3:03 pmORD-MSN
1h 03mnonstop
United Airlines Logo
4:00 pm - 5:06 pmMSN-ORD
1h 06mnonstop
$215United Airlines
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Mon, Aug 4 - Sat, Aug 9
American Airlines Logo
10:04 pm - 11:05 pmORD-MSN
1h 01mnonstop
American Airlines Logo
3:55 pm - 5:02 pmMSN-ORD
1h 07mnonstop
$223American Airlines
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Fri, Aug 1 - Sun, Aug 3
American Airlines Logo
9:03 am - 10:15 amORD-MSN
1h 12mnonstop
American Airlines Logo
8:27 pm - 9:30 pmMSN-ORD
1h 03mnonstop
$224American Airlines
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Thu, Jul 24 - Sun, Jul 27
American Airlines Logo
9:03 am - 10:15 amORD-MSN
1h 12mnonstop
American Airlines Logo
5:30 am - 6:34 amMSN-ORD
1h 04mnonstop
$229American Airlines
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Sun, Sep 7 - Thu, Sep 11
Frontier Logo
10:42 am - 7:14 pmORD-MSN
8h 32m1 stop
Frontier Logo
7:59 pm - 9:37 amMSN-ORD
13h 38m1 stop
$321Frontier
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Mon, Sep 22 - Thu, Sep 25
Frontier Logo
6:00 am - 7:14 pmORD-MSN
13h 14m1 stop
Frontier Logo
7:59 pm - 9:37 amMSN-ORD
13h 38m1 stop
$337Frontier
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Mon, Aug 4 - Sat, Aug 9
Delta Logo
12:17 pm - 8:39 amORD-MSN
20h 22m1 stop
Delta Logo
6:54 pm - 8:25 amMSN-ORD
13h 31m1 stop
$369Delta
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Sat, Nov 15 - Mon, Nov 17
Delta Logo
2:00 pm - 9:59 amMDW-MSN
19h 59m1 stop
Delta Logo
2:00 pm - 8:45 amMSN-MDW
18h 45m1 stop
$438Delta
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Good to know

Low seasonDecember
High seasonMay
Cheapest flight$131
Best time to beat the crowds with an average 39% drop in price.
Most popular time to fly with an average 40% increase in price.
Flight from Chicago O'Hare Airport to Madison

When to book flights from Chicago to Wisconsin Dells

Are your dates flexible? Find out the best times to travel from Chicago to Wisconsin Dells based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

FAQs for booking flights from Chicago to Wisconsin Dells

  • Which airports will I be using when flying from Chicago to Wisconsin Dells?

    When flying out of Chicago you’ll be using one of these airports: Chicago Midway or Chicago O'Hare Intl. Wisconsin Dells does not have its own airport so you’ll be flying into nearby Madison Truax Field airport, which is 40.6 mi away.

  • How long does a flight from Chicago to Wisconsin Dells take?

    Direct flights cover the 123 miles separating Chicago and Wisconsin Dells in about 1h 00m.

  • How many flights are there between Chicago and Wisconsin Dells?

    59 direct flights run between Chicago and Wisconsin Dells on a daily basis. On average, there are about 416 departures each week.

  • What’s the cheapest day of the week to fly between Chicago and Wisconsin Dells?

    Consider leaving on a Thursday and avoid Mondays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Thursdays and the most expensive ones on Sundays.

  • How does KAYAK find such low prices on flights from Chicago to Wisconsin Dells?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Wisconsin Dells.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Wisconsin Dells?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Wisconsin Dells from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Wisconsin Dells?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Wisconsin Dells with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Wisconsin Dells?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Wisconsin Dells from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • Which airlines provide the cheapest flights from Chicago to Wisconsin Dells?

    In the last 72 hours, the cheapest one-way ticket between Chicago and Wisconsin Dells found on KAYAK was with Frontier for $131. United Airlines offered a round-trip connection from $179 and American Airlines from $180.

Top tips for finding cheap flights from Chicago to Wisconsin Dells

  • There is no airport in Wisconsin Dells. Instead, you’ll be flying into Madison Truax Field Airport when flying between Chicago and Wisconsin Dells.
  • High season is considered to be March, April and May. The cheapest month to fly is December.

Reviews of the top airline flying from Chicago to Wisconsin Dells

 
Need help choosing which airline to fly with from Chicago to Wisconsin Dells? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.4
United AirlinesOverall score based on 8846 reviews
8.1Crew
6.6Food
7.7Boarding
7.3Comfort
7.0Entertainment
Airline reviews

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

8.0 ExcellentAnonymous, Jul 2025ORD - SUX
Read more United Airlines reviews

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

Everything you need to know for your flight from Chicago to Wisconsin Dells

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