$124 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 2/25. 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
$179
American Airlines
Fri 12/19Sun 12/28
ORD - MSN • Non-stop
Cheapest one-way
$129
Typical prices: $267-$279
Multiple Airlines
Wed 2/25
ORD - MSN • 1 stop
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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

Fri, Dec 19 - Sun, Dec 28
American Airlines Logo
4:38 pm - 5:41 pmORD-MSN
1h 03mnonstop
American Airlines Logo
8:10 pm - 9:30 pmMSN-ORD
1h 20mnonstop
$179American Airlines
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Sun, Jan 11 - Sun, Jan 18
American Airlines Logo
5:40 pm - 6:44 pmORD-MSN
1h 04mnonstop
American Airlines Logo
11:25 am - 12:44 pmMSN-ORD
1h 19mnonstop
$180American Airlines
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Thu, Dec 18 - Sun, Dec 21
American Airlines Logo
10:30 pm - 11:37 pmORD-MSN
1h 07mnonstop
American Airlines Logo
8:10 pm - 9:30 pmMSN-ORD
1h 20mnonstop
$181American Airlines
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Thu, Dec 11 - Mon, Dec 15
American Airlines Logo
8:15 am - 9:19 amORD-MSN
1h 04mnonstop
American Airlines Logo
8:08 pm - 9:29 pmMSN-ORD
1h 21mnonstop
$209American Airlines
Find Deal
Wed, Jan 14 - Sat, Jan 17
United Airlines Logo
8:00 pm - 9:05 pmORD-MSN
1h 05mnonstop
United Airlines Logo
5:26 pm - 6:47 pmMSN-ORD
1h 21mnonstop
$239United Airlines
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Thu, Dec 18 - Sun, Dec 21
United Airlines Logo
10:35 am - 11:48 amORD-MSN
1h 13mnonstop
United Airlines Logo
8:15 am - 9:36 amMSN-ORD
1h 21mnonstop
$241United Airlines
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Sun, Jan 11 - Sun, Jan 18
Multiple Airlines Logo
7:00 am - 5:40 pmORD-MSN
10h 40m1 stop
Multiple Airlines Logo
6:40 pm - 9:43 amMSN-ORD
15h 03m1 stop
$272Multiple Airlines
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Wed, Dec 10 - Sat, Dec 13
Delta Logo
6:40 pm - 12:50 pmMDW-MSN
18h 10m1 stop
Delta Logo
6:59 am - 6:06 pmMSN-MDW
11h 07m1 stop
$619Delta
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Sun, Dec 28 - Wed, Dec 31
Multiple Airlines Logo
10:50 pm - 2:01 pmMDW-MSN
15h 11m1 stop
Multiple Airlines Logo
6:08 pm - 5:38 pmMSN-MDW
23h 30m2 stops
$669Multiple Airlines
Find Deal
Thu, Dec 18 - Sun, Dec 21
Delta Logo
9:34 am - 5:38 pmMDW-MSN
8h 04m1 stop
Delta Logo
7:00 am - 5:26 pmMSN-MDW
10h 26m1 stop
$778Delta
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Good to know

Low seasonDecember
Cheapest flight$129
Best time to beat the crowds with an average 48% drop in price.
Most popular time to fly and prices are also 18% lower on average.
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 56m.

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

    64 direct flights run between Chicago and Wisconsin Dells on a daily basis. On average, there are about 453 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 Tuesdays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Wednesdays and the most expensive ones on Thursdays.

  • 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 9058 reviews
8.1Crew
7.1Entertainment
7.3Comfort
7.7Boarding
6.6Food
Airline reviews

Very thoughtful flight attendant offered me water immediately since I had run to make my connection.

10.0 ExcellentJeremy, Nov 2025ORD - DCA
Read more United Airlines reviews

Very thoughtful flight attendant offered me water immediately since I had run to make my connection.

Always wish for more healthy, gluten free options. We have to bring our own.

Having a long layover, I was very appreciative of the ability to stand by for an earlier flight. Other airlines like Delta have refused this to me in the past, just to be mean (because my ticket class wasn't high enough). United went out of their way to help me get to my destination early, which I really appreciated given that it was the third leg of a 24+ hour journey for me.

Other than a way way too cold cabinets for the entire flight, all was great

One bag is incorrect and not acceptable for an international flight. The food was not just good. I won't fly with them again.

Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.

I will never book a flight through Cheap fare. They booked me from Portland Main . And would not give me a refund, so I bought 2 tickets one for 299. From Portland Main to ORD. Then I had to buy a ticket from Oregon PDX to ORD that was another 440. So Just so you know they even told me it was there fault but no refund. Bad bussniess. I did inform United but they said they couldn't help me due to the fact I booked through Cheap Tickets. Never again. And I'm spreding the word. I let everyone know at my 50th class reunion

Crew and customer service were excellent. This flight also had plenty of leg room and seat mounted screens for entertainment. A very pleasant flight all around!

It would have been better if the crew has supported my husband's reasons for needing to keep the space clear around his feet, rather than insisting that he put his knapsack in that space.

Subject: Formal Complaint: Discriminatory and Unprofessional Conduct – Request for Immediate Action & Compensation Dear [Airline Customer Relations Team], I am writing to file a formal complaint regarding my recent travel experience with [Airline], which was by far the worst I have ever encountered. What occurred was not only unprofessional, but in several instances discriminatory, unsafe, and unacceptable. On the first leg of my trip, I arrived only four minutes past check-in. Instead of making any attempt to resolve the matter, your representative flatly denied me boarding and made me wait while she attended to passengers who arrived after me. By the time a manager intervened, it was too late to board, costing me time, money, and unnecessary frustration. The second leg of my trip (Chicago–San Francisco) raised even more serious concerns. From the outset, it was apparent that the staff—particularly two attendants—prioritized Caucasian passengers while dismissing African American and minority passengers. • When a Caucasian passenger in the exit row refused to comply with federal safety requirements, I, as a first responder, immediately offered to switch seats and assume the responsibility. My offer was blatantly ignored, and instead, a Caucasian passenger seated further up was chosen. This was discriminatory and deeply insulting, especially as I was actively de-escalating the situation that could have delayed the flight further. • During a lengthy tarmac delay of over 90 minutes, passengers were given conflicting and unreasonable instructions that created unnecessary distress and tension. • Throughout the flight, a visibly intoxicated passenger directly in front of me was disruptive, rude to others, failed to comply with seatbelt and electronic device rules, and yet faced no enforcement from the crew. In stark contrast, I was singled out for repeated compliance checks even though I was following every rule. This unequal treatment was so obvious that multiple passengers around me spoke up in my defense. This pattern of behavior demonstrated a clear lack of professionalism, disregard for passenger safety, and discriminatory treatment. I expect far better from an airline of your stature. As a paying customer subjected to this unacceptable treatment, I am formally requesting: 1. A full investigation into the conduct of the staff on both flights. 2. A written apology acknowledging the discriminatory and unprofessional behavior I endured. 3. Appropriate compensation for the distress, inconvenience, and mishandling of my travel. If this matter is not addressed promptly and thoroughly, I will have no choice but to escalate my complaint further, including filing with the U.S. Department of Transportation and sharing my experience through other channels. I trust [Airline] will take this complaint seriously and provide a timely resolution.

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