$116 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 5/10. 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, 0 bags

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Everything you should know

Cheapest round-trip
$239
American Airlines
Thu 5/7Sun 5/10
ORD - MSN • Non-stop
Cheapest non-stop
$239
American Airlines
Sat 5/9Sat 5/16
ORD - MSN • Non-stop
Arrival airport
You can't fly directly to Wisconsin Dells. It is served by Madison (MSN), located 40.6 miles from Wisconsin Dells.
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Flight Deals
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Flight Deals

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, May 7 - Sun, May 10
American Airlines Logo
8:40 am - 9:48 am
ORD
-
MSN
1h 08mnonstop
American Airlines Logo
8:24 pm - 9:40 pm
MSN
-
ORD
1h 16mnonstop
$239American Airlines
Fri, May 1 - Sun, May 3
American Airlines Logo
6:41 pm - 7:54 pm
ORD
-
MSN
1h 13mnonstop
American Airlines Logo
9:18 am - 10:31 am
MSN
-
ORD
1h 13mnonstop
$240American Airlines
Thu, May 7 - Sun, May 10
American Airlines Logo
7:39 am - 8:45 am
ORD
-
MSN
1h 06mnonstop
American Airlines Logo
8:24 pm - 9:40 pm
MSN
-
ORD
1h 16mnonstop
$249American Airlines
Fri, May 1 - Sun, May 3
American Airlines Logo
6:41 pm - 7:54 pm
ORD
-
MSN
1h 13mnonstop
American Airlines Logo
5:30 am - 6:47 am
MSN
-
ORD
1h 17mnonstop
$254American Airlines
Thu, Aug 6 - Sun, Aug 16
American Airlines Logo
8:20 am - 9:22 am
ORD
-
MSN
1h 02mnonstop
American Airlines Logo
6:00 am - 7:06 am
MSN
-
ORD
1h 06mnonstop
$258American Airlines
Mon, May 4 - Mon, May 11
American Airlines Logo
8:58 pm - 10:10 pm
ORD
-
MSN
1h 12mnonstop
American Airlines Logo
8:24 pm - 9:40 pm
MSN
-
ORD
1h 16mnonstop
$259American Airlines
Sat, Apr 25 - Wed, Apr 29
American Airlines Logo
8:40 am - 9:48 am
ORD
-
MSN
1h 08mnonstop
American Airlines Logo
2:18 pm - 3:38 pm
MSN
-
ORD
1h 20mnonstop
$269American Airlines
Thu, Aug 6 - Sun, Aug 16
American Airlines Logo
6:40 pm - 11:57 pm
ORD
-
MSN
5h 17m
1 stop
American Airlines Logo
6:00 am - 7:06 am
MSN
-
ORD
1h 06mnonstop
$277American Airlines
Sat, May 9 - Sat, May 16
Multiple Airlines Logo
9:37 pm - 8:25 am
ORD
-
MSN
34h 48m
2 stops
Multiple Airlines Logo
9:54 am - 12:23 pm
MSN
-
ORD
26h 29m
1 stop
$294Multiple Airlines
Sat, May 23 - Tue, May 26
United Airlines Logo
10:25 am - 11:38 am
ORD
-
MSN
1h 13mnonstop
United Airlines Logo
6:30 am - 7:40 am
MSN
-
ORD
1h 10mnonstop
$309United Airlines
Useful Info

Good to know

Low seasonDecember
Cheapest flight$116
Best time to beat the crowds with an average 38% drop in price.
Most popular time to fly with an average 21% 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 59m.

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

    92 direct flights run between Chicago and Wisconsin Dells on a daily basis. On average, there are about 648 departures each week.

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

    Consider leaving on a Wednesday and avoid Sundays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Fridays 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.

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 9589 reviews
7.7Boarding
7.1Entertainment
6.6Food
8.1Crew
7.3Comfort
Airline reviews

Poor communication, flight was delayed for preventable reasons. I missed my connection.

2.0 MediocreAaron, Apr 2026
ORD - BNA
Read more United Airlines reviews

Poor communication, flight was delayed for preventable reasons. I missed my connection.

No meal service to the back of the plane as it started late or was too slow to get it out before it was time to land.

Terrible, if possible won't be flying again anytime soon!

Efficient boarding and early departure. Very smooth flight. Early arrival in ATL. Great flight.

Smooth and easy boarding, comfortable for the entire 5 hour flight, and the seat back entertainment was great! I appreciated all the features, from location info and maps, movies, the ability to connect with Bluetooth headphones, and good selection of movies. Food was good, normal airline snacks (I didn’t purchase anything)

Awful. No counter attendants. No dinner offered due to delays.

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

We were delayed for about an hour from taking off due to traffic control procedures at the destination airport. But once in the air, the flight went well. The crew members were great and provided cabin service despite moderate turbulence during much of the flight.

Short flight, but no drink/snack service. The flights both going and coming were delayed.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

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

Complete your trip to Wisconsin Dells with a hotel stay or car rental