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Cheap Flights from Chicago to Wisconsin Dells

Compare Chicago to Wisconsin Dells flight deals

Find the cheapest month or even day of the year to fly to Wisconsin Dells

Book the best Wisconsin Dells fare with no extra fees

Flight deals from Chicago to Wisconsin Dells

Looking for a cheap last-minute deal or the best return flight from Chicago to Wisconsin Dells? Find the lowest prices on one-way and return tickets right here.
Madison.893 zł per passenger.Departing Sat, 9 Jan, returning Sat, 23 Jan.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Sat, 9 Jan, arriving in Madison.Inbound direct flight with United departs from Madison on Sat, 23 Jan, arriving in Chicago O'Hare International.Price includes taxes and charges.From 893 zł, select.
Madison.895 zł per passenger.Departing Fri, 9 Oct, returning Sun, 11 Oct.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Fri, 9 Oct, arriving in Madison.Inbound direct flight with United departs from Madison on Sun, 11 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From 895 zł, select.
Madison.899 zł per passenger.Departing Sat, 18 Jul, returning Sun, 19 Jul.Return flight with American Airlines.Outbound direct flight with American Airlines departs from Chicago O'Hare International on Sat, 18 Jul, arriving in Madison.Inbound direct flight with American Airlines departs from Madison on Sun, 19 Jul, arriving in Chicago O'Hare International.Price includes taxes and charges.From 899 zł, select.
Madison.900 zł per passenger.Departing Sun, 9 Aug, returning Sun, 16 Aug.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Sun, 9 Aug, arriving in Madison.Inbound direct flight with United departs from Madison on Sun, 16 Aug, arriving in Chicago O'Hare International.Price includes taxes and charges.From 900 zł, select.
Madison.900 zł per passenger.Departing Tue, 15 Sep, returning Tue, 22 Sep.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Tue, 15 Sep, arriving in Madison.Inbound direct flight with United departs from Madison on Tue, 22 Sep, arriving in Chicago O'Hare International.Price includes taxes and charges.From 900 zł, select.
Madison.900 zł per passenger.Departing Tue, 11 Aug, returning Tue, 1 Sep.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Tue, 11 Aug, arriving in Madison.Inbound direct flight with United departs from Madison on Tue, 1 Sep, arriving in Chicago O'Hare International.Price includes taxes and charges.From 900 zł, select.
Madison.1 142 zł per passenger.Departing Sun, 13 Dec, returning Sun, 20 Dec.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Sun, 13 Dec, arriving in Madison.Inbound direct flight with United departs from Madison on Sun, 20 Dec, arriving in Chicago O'Hare International.Price includes taxes and charges.From 1 142 zł, select.
Madison.1 155 zł per passenger.Departing Fri, 23 Apr, returning Mon, 26 Apr.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Fri, 23 Apr, arriving in Madison.Inbound direct flight with United departs from Madison on Mon, 26 Apr, arriving in Chicago O'Hare International.Price includes taxes and charges.From 1 155 zł, select.
Madison.1 201 zł per passenger.Departing Thu, 27 Aug, returning Fri, 18 Dec.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Thu, 27 Aug, arriving in Madison.Inbound direct flight with United departs from Madison on Fri, 18 Dec, arriving in Chicago O'Hare International.Price includes taxes and charges.From 1 201 zł, select.
Madison.1 276 zł per passenger.Departing Fri, 7 May, returning Mon, 10 May.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Fri, 7 May, arriving in Madison.Inbound direct flight with United departs from Madison on Mon, 10 May, arriving in Chicago O'Hare International.Price includes taxes and charges.From 1 276 zł, select.
Madison.1 293 zł per passenger.Departing Sun, 26 Jul, returning Sat, 1 Aug.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Sun, 26 Jul, arriving in Madison.Inbound direct flight with United departs from Madison on Sat, 1 Aug, arriving in Chicago O'Hare International.Price includes taxes and charges.From 1 293 zł, select.
Madison.2 023 zł per passenger.Departing Mon, 8 Feb, returning Tue, 9 Feb.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Mon, 8 Feb, arriving in Madison.Inbound direct flight with United departs from Madison on Tue, 9 Feb, arriving in Chicago O'Hare International.Price includes taxes and charges.From 2 023 zł, select.
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Chicago to Wisconsin Dells: Flight information

The things to know before you go.
Fly intoMadison Airport
Distance to Wisconsin Dells64.6 km
Cheapest flight893 zł
Cheapest month to flyJanuary
Most popular airlineAmerican Airlines
Average flight time1 hr, 10 mins

Find the cheapest month to fly from Chicago to Wisconsin Dells

We’re always keeping an eye on fares, so you can find the best flight deal in seconds. It looks like Chicago to Wisconsin Dells flights are currently cheapest in September. We’ve based this on flights into Madison Airport.
Jun
from 1 331 zł
Jul
from 699 zł
Aug
from 493 zł
Sep
from 422 zł
Oct
from 879 zł
Nov
from 879 zł
Dec
from 873 zł
Jan
Find prices
Feb
Find prices
Mar
Find prices
Apr
Find prices
May
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Finding cheap flights from Chicago to Wisconsin Dells: Frequently asked questions

There are 2 airports near Wisconsin Dells: Madison Airport and Milwaukee General Mitchell Airport.
The best price we found for a return flight from Chicago to Wisconsin Dells is 893 zł. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
American Airlines, United, Alaska Airlines all offer direct flights to Madison Airport.
We've checked every Chicago to Wisconsin Dells fare we could find, and the cheapest upcoming date to fly seems to be on Saturday, 9 January 2027. Overall, the cheapest month to fly from Chicago to Wisconsin Dells is usually January.
If you're flying from Chicago, the cheapest airport near Wisconsin Dells is Madison – which is 64.6 km away from the centre of Wisconsin Dells. We've found flights into this airport from 893 zł.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Wisconsin Dells on Saturday, 9 January 2027.
No airlines currently offer direct flights between Chicago and Wisconsin Dells. Most routes have one or more stops.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Wisconsin Dells but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Wisconsin Dells is around 40 days in advance, so don’t leave your flight to the last minute.

Madison Airport is 64.6km from Wisconsin Dells and Milwaukee General Mitchell Airport is 169.7km from Wisconsin Dells.
Madison Airport is closest to Wisconsin Dells, at around 64.6 km away.
The cheapest airline that flies to Wisconsin Dells is United .