$114 Find Cheap Flights from Colorado Springs to Wisconsin - Compare and Save

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Cheap Flights from Colorado Springs to Wisconsin

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Milwaukee
Milwaukee1 stop$240
Madison
Madison1 stop$339
Appleton
Appleton1 stop$449
Green Bay
Green Bay1 stop$349
Wausau
Wausau2 stops$484
Minneapolis
Minneapolis1 stop$218
Chicago
Chicagononstop$253
Duluth
Duluth2 stops$454
Milwaukee
Milwaukee1 stop$240
Madison
Madison1 stop$339
Appleton
Appleton1 stop$449
Green Bay
Green Bay1 stop$349
Wausau
Wausau2 stops$484
Minneapolis
Minneapolis1 stop$218
Chicago
Chicagononstop$253
Duluth
Duluth2 stops$454
Booking Insights

KAYAK's insights & trends for Colorado Springs to Wisconsin flights

Get data-powered insights and trends into flights from Colorado Springs to Wisconsin to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Colorado Springs to Wisconsin?

Flight prices are below average for this route right now.

Flights to Wisconsin from Colorado Springs usually cost between $366 and $594 in January.
The lowest price found in the past 5 days was $240 on United Airlines (Jan 14-Jan 18).

What is the cheapest month to fly from Colorado Springs to Wisconsin?

The cheapest month for flights from Colorado Springs to Wisconsin is July, when tickets cost $265 (return) on average. On the other hand, the most expensive months are October and December, when the average cost of round-trip tickets is $494 and $468 respectively.

Good to know

Low season

January

Cheapest flight

$114
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly with an average 21% increase in price.
Flight from Colorado Springs to Milwaukee

FAQs - booking Wisconsin flights

  • How does KAYAK find such low prices on flights from Colorado Springs to Wisconsin?

    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 Colorado Springs to Wisconsin.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Colorado Springs to Wisconsin?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Colorado Springs to Wisconsin 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 Colorado Springs to Wisconsin?

    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 from Colorado Springs to Wisconsin with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Colorado Springs to Wisconsin?

    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 from Colorado Springs to Wisconsin 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 to Wisconsin

  • Looking for a cheap flight? 25% of our users found tickets from Colorado Springs to the following destinations at these prices or less: Chicago $249 one-way - $387 round-trip

Reviews of the top 3 airlines serving from Colorado Springs to Wisconsin

 
Need help choosing which airline to fly with from Colorado Springs to Wisconsin? 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.
7.9
SouthwestOverall score based on 4220 reviews
8.1Boarding
8.6Crew
8.0Comfort
7.0Food
7.4Entertainment
Airline reviews

I fly out every other weekend and this is the 4th time my flight has been delayed at Southwest. I will be flying out twice a month on average for the next 6-7 months. If this is your average ‘on time’ I’ll probably be flying another airline.

8.0 ExcellentDelores, Oct 2026
Read more Southwest reviews

I fly out every other weekend and this is the 4th time my flight has been delayed at Southwest. I will be flying out twice a month on average for the next 6-7 months. If this is your average ‘on time’ I’ll probably be flying another airline.

WiFi was inoperable - second in four recent Southwest flights where that was true. I need WiFi for work and if Southwest cannot provide, I’ll stop using it

A List preferred boarding was nice Asked for a mask and cheerfully received Denver bag check-in is tricky. Not near other checking desk. Have to navigate to east security and up to level six for bag checkin. TSA busy and 20 minutes process thru pre lines Denver train to gates quick but one more thing to plan time for and long concourse walk to gate

Southwest has inacted unfriendly customer policies like other airlines. Watch the fine print very carefully if you are having to alter flight arrangements. Rules are now complicated and very stilted to travelers sacrificing travel funds (unlike before where the simple, straight forward flight change policy was worth the extra premium for ticket price.) On the positive side, SW Flight crews are still wonderfully helpful.

Slow boarding, limited food and drink portions. Bad delays and turbulence

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

The entire travel day was a disaster from beginning to end. Woke up at two in the morning to make it to San Juan airport in time for a 5:30 am flight to Milwaukee which connected in Baltimore. Massive delays lead to me missing original connection out of Baltimore. Sixteen hours of delays/rebooking/layover time later, arrived in Milwaukee to find that only one of two checked bags made it there (despite the fact that Southwest brought another 737 jet to San Juan to fly us out to our original Baltimore connection—-not squeezed into another booked flight). The flight from Baltimore to Milwaukee was barely half full, so there was no logical reason to ship my bags out of Baltimore on a different flight to Chicago to then ship to Milwaukee. Southwest decided that my bags should not have been on the same connecting flight I WAS ON to Milwaukee, and then proceeded to accidentally leave my larger bag with the important items in Chicago. Terrible logic and support all around. Extremely angered and disappointed with SW. What a clownish operation your company has become!

Great no problem boarding suitcase on time for pick up

Delay after delay after delay. Very disappointing I am about ready to give up on Southwest. One of the crewmembers sat and played games on her phone for the entire trip from Chicago to Baltimore. Unbelievable, very unprofessional, and very disappointing.

I've never flown Southwest before and I can say its my new favorite airline.

Gate agents call groups one and two and give about 3-5 minutes for each group to board, then the call groups three and four together and it causes a bottleneck in the line. Give each group 3-5 minutes to board before calling the next group.

All was fine. Small plane so no food or entertainment.

Mechanical Delay of over an hour with multiple gate changes. Entertainment system down for rejuvenation.

Love delta smaller commuter plane so no entertainment and paid wifi on MKE-LGA leg was extremely unreliable and slow

My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.

The seats got pretty uncomfortable pretty fast. The armrests are bigger than on other planes, so I had less room in the actual seat. My butt hurt by the end of the flight. :/ comfort was the primary issue. The crew were fantastic!

The dear was very limited in space. I could put my water bottle in seat basket. Also, there was no inflight entertainment in the delta app?

Wifi did not work and they only served water, coffee, or tea.

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Had assistance at airport getting from arrivals gate to departure gate; I couldn't have managed without that extra help. Thank you Delta.

The guy in front of me was talking constantly, even when the pilot was making announcements. I found this very disrespectful to the pilot and to others.

Really delayed, no effort to support customers other than “sometimes we run late.”

Both of my flights arrived early and check in process was smooth

Deplaning was delayed because of Jetbridge equipment issues in MKE, causing an issue on an otherwise great flight.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

Flight home lot's of room shame I never noticed that they ripped my suitcase and didn't notice it to I got toy destination and had to buy new set

No real agent onsite helping you for missing luggage there. Not like the other airline next to UA desk, they have staff attending in their desk assisting answer/helping luggage issue, even after midnight.

It was delayed several hours which delayed our connection in Denver. Not happy.

The wi-fi was awful. I paid $8 each way and got little , except frustration. .

Ridiculous delays with weak excuses. United needs to do their job and troubleshoot. The rate they charge demands no less. Planes are way too full and seats are cramped. Charging for seats and luggage adds insult to injury.

More options for your flight from Colorado Springs to Wisconsin

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