$134 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 3/31. 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
$178
American Airlines
Thu 2/26Sun 3/1
ORD - MSN • Non-stop
Cheapest one-way
$134
Typical prices: $154-$279
American Airlines
Tue 3/31
ORD - MSN • Non-stop
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Flight Deals
Useful Info
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, Feb 26 - Sun, Mar 1
American Airlines Logo
8:05 am - 9:11 am
ORD
-
MSN
1h 06mnonstop
American Airlines Logo
8:24 pm - 9:31 pm
MSN
-
ORD
1h 07mnonstop
$178American Airlines
Mon, Mar 2 - Mon, Mar 9
American Airlines Logo
8:05 am - 9:11 am
ORD
-
MSN
1h 06mnonstop
American Airlines Logo
8:24 pm - 9:31 pm
MSN
-
ORD
1h 07mnonstop
$179American Airlines
Fri, Feb 20 - Mon, Feb 23
American Airlines Logo
7:50 pm - 8:56 pm
ORD
-
MSN
1h 06mnonstop
American Airlines Logo
8:24 pm - 9:31 pm
MSN
-
ORD
1h 07mnonstop
$194American Airlines
Wed, Feb 18 - Sun, Feb 22
American Airlines Logo
8:05 am - 9:11 am
ORD
-
MSN
1h 06mnonstop
American Airlines Logo
8:24 pm - 9:31 pm
MSN
-
ORD
1h 07mnonstop
$209American Airlines
Fri, Feb 13 - Sun, Feb 15
United Airlines Logo
8:04 pm - 9:07 pm
ORD
-
MSN
1h 03mnonstop
United Airlines Logo
8:15 am - 9:27 am
MSN
-
ORD
1h 12mnonstop
$224United Airlines
Wed, Feb 11 - Sat, Feb 14
American Airlines Logo
11:41 am - 12:46 pm
ORD
-
MSN
1h 05mnonstop
American Airlines Logo
3:03 pm - 4:10 pm
MSN
-
ORD
1h 07mnonstop
$239American Airlines
Fri, Feb 20 - Tue, Feb 24
United Airlines Logo
6:00 pm - 6:58 pm
ORD
-
MSN
0h 58mnonstop
United Airlines Logo
8:15 am - 9:27 am
MSN
-
ORD
1h 12mnonstop
$254United Airlines
Tue, Feb 17 - Sat, Feb 21
United Airlines Logo
9:06 am - 10:14 am
ORD
-
MSN
1h 08mnonstop
United Airlines Logo
2:48 pm - 4:00 pm
MSN
-
ORD
1h 12mnonstop
$269United Airlines
Thu, Feb 26 - Sun, Mar 1
American Airlines Logo
5:00 am - 10:36 am
ORD
-
MSN
5h 36m
1 stop
American Airlines Logo
8:24 pm - 9:31 pm
MSN
-
ORD
1h 07mnonstop
$276American Airlines
Mon, Mar 23 - Sun, Mar 29
Multiple Airlines Logo
9:51 pm - 5:21 pm
MDW
-
MSN
19h 30m
1 stop
Multiple Airlines Logo
7:45 pm - 10:19 pm
MSN
-
MDW
26h 34m
2 stops
$557Multiple Airlines
Useful Info

Good to know

Low seasonDecember
Cheapest flight$134
Best time to beat the crowds with an average 42% drop in price.
Most popular time to fly with an average 19% 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 57m.

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

    63 direct flights run between Chicago and Wisconsin Dells on a daily basis. On average, there are about 445 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 9236 reviews
7.1Entertainment
7.7Boarding
7.3Comfort
8.1Crew
6.6Food
Airline reviews

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

2.0 MediocreRonald, Feb 2026
ORD - BWI
Read more United Airlines reviews

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

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

I liked the snacks and the flight attendants were friendly.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

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

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