$130 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 10/30. 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

Sat, Nov 8 - Sat, Nov 15
American Airlines Logo
8:15 am - 9:18 amORD-MSN
1h 03mnonstop
American Airlines Logo
9:48 am - 11:02 amMSN-ORD
1h 14mnonstop
$179American Airlines
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Wed, Nov 26 - Wed, Dec 3
American Airlines Logo
9:15 pm - 10:23 pmORD-MSN
1h 08mnonstop
American Airlines Logo
4:39 pm - 5:57 pmMSN-ORD
1h 18mnonstop
$180American Airlines
Find Deal
Sat, Mar 14 - Tue, Mar 17
United Airlines Logo
7:52 pm - 8:55 pmORD-MSN
1h 03mnonstop
United Airlines Logo
3:58 pm - 5:10 pmMSN-ORD
1h 12mnonstop
$239United Airlines
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Fri, Oct 24 - Mon, Oct 27
United Airlines Logo
12:50 pm - 1:50 pmORD-MSN
1h 00mnonstop
United Airlines Logo
6:30 am - 7:41 amMSN-ORD
1h 11mnonstop
$249United Airlines
Find Deal
Mon, Oct 27 - Fri, Oct 31
Frontier Logo
12:11 pm - 7:14 pmMDW-MSN
7h 03m1 stop
Frontier Logo
8:00 pm - 9:35 pmMSN-MDW
25h 35m2 stops
$256Frontier
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Sat, Nov 8 - Sat, Nov 15
Multiple Airlines Logo
6:48 am - 5:28 pmORD-MSN
10h 40m1 stop
Multiple Airlines Logo
9:48 am - 11:29 pmMSN-ORD
13h 41m2 stops
$293Multiple Airlines
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Sat, Nov 8 - Sat, Nov 15
Multiple Airlines Logo
6:48 am - 5:28 pmORD-MSN
10h 40m1 stop
Multiple Airlines Logo
9:48 am - 11:29 pmMSN-ORD
13h 41m2 stops
$304Multiple Airlines
Find Deal
Sun, Oct 26 - Thu, Oct 30
Frontier Logo
5:20 am - 7:14 pmMDW-MSN
37h 54m2 stops
Frontier Logo
8:00 pm - 11:30 amMSN-MDW
15h 30m1 stop
$315Frontier
Find Deal
Sat, Mar 14 - Tue, Mar 17
Delta Logo
9:20 am - 10:08 pmMDW-MSN
12h 48m1 stop
Delta Logo
6:15 am - 1:08 pmMSN-MDW
6h 53m1 stop
$452Delta
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Sat, Mar 14 - Tue, Mar 17
Delta Logo
9:30 am - 10:08 pmMDW-MSN
12h 38m2 stops
Delta Logo
6:15 am - 1:08 pmMSN-MDW
6h 53m1 stop
$475Delta
Find Deal

Everything you should know

Cheapest round-trip
$179
American Airlines
Sat 11/8Sat 11/15
ORD - MSN • Non-stop
Cheapest one-way
$130
Typical prices: $274-$422
Frontier
Thu 10/30
ORD - MSN • 1 stop
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We hope you love your trip to Wisconsin Dells!
Useful Info

Good to know

Low seasonJune
Cheapest flight$130
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly and prices are also 16% 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 59m.

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

    68 direct flights run between Chicago and Wisconsin Dells on a daily basis. On average, there are about 478 departures each week.

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

    Consider leaving on a Saturday and avoid Fridays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Tuesdays 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 Frontier for $130. American Airlines offered a round-trip connection from $179 and United Airlines from $239.

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 8970 reviews
7.7Boarding
6.6Food
7.3Comfort
7.1Entertainment
8.1Crew
Airline reviews

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

8.0 ExcellentCynthia, Oct 2025ORD - PDX
Read more United Airlines reviews

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.

Check in was quick and easy during early hours. Flight was on time, and customer services was a plus.

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

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

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

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