$179 Find Cheap Flights from Chicago to Wisconsin Dells

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Wisconsin Dells departing on 5/29. 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.
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Cheap Flight Deals 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.

Recent round-trip flight deals from Chicago to Wisconsin Dells

KAYAK's recommended round-trip deals from the most popular airlines that fly from Chicago to Wisconsin Dells.
Discover the best prices for you by selecting your travel dates on KAYAK.
American Airlines Logo
7:00 am - 8:01 amORD-MSN
1h 01mnonstop
American Airlines Logo
8:16 pm - 9:19 pmMSN-ORD
1h 03mnonstop
$179American Airlines
Find Deal
Thu, May 29 - Thu, Jun 5
American Airlines Logo
7:00 am - 8:01 amORD-MSN
1h 01mnonstop
American Airlines Logo
10:39 am - 11:46 amMSN-ORD
1h 07mnonstop
$180American Airlines
Find Deal
Thu, May 22 - Sun, May 25
American Airlines Logo
9:00 am - 10:12 amORD-MSN
1h 12mnonstop
American Airlines Logo
8:27 pm - 9:30 pmMSN-ORD
1h 03mnonstop
$183American Airlines
Find Deal
Thu, Jul 31 - Sun, Aug 3
American Airlines Logo
10:21 am - 11:19 amORD-MSN
0h 58mnonstop
American Airlines Logo
3:28 pm - 4:29 pmMSN-ORD
1h 01mnonstop
$189American Airlines
Find Deal
Thu, May 15 - Tue, May 20
United Airlines Logo
7:45 pm - 8:58 pmORD-MSN
1h 13mnonstop
United Airlines Logo
2:35 pm - 3:45 pmMSN-ORD
1h 10mnonstop
$254United Airlines
Find Deal
Sat, Jul 12 - Wed, Jul 16
American Airlines Logo
8:16 am - 9:20 amORD-MSN
1h 04mnonstop
American Airlines Logo
5:40 am - 6:41 amMSN-ORD
1h 01mnonstop
$269American Airlines
Find Deal
Thu, Jun 19 - Sun, Jun 22
United Airlines Logo
2:10 pm - 3:17 pmORD-MSN
1h 07mnonstop
United Airlines Logo
6:30 am - 7:33 amMSN-ORD
1h 03mnonstop
$289United Airlines
Find Deal
Thu, May 15 - Mon, May 19
 Logo
6:30 am - 8:01 amORD-MSN
25h 31m1 stop
 Logo
8:46 am - 6:42 amMSN-ORD
21h 56m1 stop
Tue, Jun 3 - Sat, Jun 7
 Logo
6:30 am - 8:01 amORD-MSN
25h 31m1 stop
 Logo
8:46 am - 5:25 amMSN-ORD
20h 39m2 stops
Tue, Jun 3 - Sat, Jun 7
Delta Logo
1:45 pm - 8:43 pmORD-MSN
6h 58m1 stop
Delta Logo
7:00 am - 8:21 pmMSN-ORD
13h 21m1 stop
$629Delta
Find Deal
Thu, May 22 - Sun, May 25
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Good to know

Low seasonDecember
High seasonMay
Cheapest flight$179
Best time to beat the crowds with an average 37% drop in price.
Most popular time to fly with an average 18% 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 0h 58m.

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

    60 direct flights run between Chicago and Wisconsin Dells on a daily basis. On average, there are about 423 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 Tuesdays 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 Fridays.

  • 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 American Airlines for $204. American Airlines offered a round-trip connection from $179 and United Airlines from $254.

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.

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 8696 reviews
8.1Crew
7.3Comfort
6.6Food
7.1Entertainment
7.7Boarding
Airline reviews

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

8.0 ExcellentAnonymous, Apr 2025ORD - SFO
Read more United Airlines reviews

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

Our seats were all the way in back of the plane,

The seats on this flight were almost roomy enough to be the basic amount needed for human existence. I think my favorite part of this flight was it landed at an A gate, which was the most palatial part of Sea-Tac I've ever seen - a massive improvement from the S gates.

The seats on this flight were almost roomy enough to be the basic amount needed for human existence.

The flight attendants in First Class were mediocre at best. They did not take our tray away until we were about to land and only did so when I press the call button. The United person at the United Club was asked to get us our boarding pass since we missed the flight due in Chicago. She argued that we did not have seats on the flight given to us in Moline. Furthermore, she was adamant that we did not have a First Class ticket. After I spent much time with her trying to show we were correct, she reluctantly agreed. She was probably the most incompetent ticketing person I have ever met and I have traveled 3 million miles on United plus many additional miles with other carriers. United has definitely deteriorated in more than on way.

Short flight - no food understandable. Flight was delayed for over an hour. Overall, it was good.

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

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