$147 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
Sort by: Cheapest
Milwaukee
4h 10m2 stops
from $285per person
Chicago
2h 34mNonstop
from $293per person
Minneapolis
3h 51m2 stops
from $319per person
Madison
4h 26m2 stops
from $319per person
Appleton
5h 03m2 stops
from $342per person
Green Bay
5h 57m2 stops
from $419per person
Duluth
5h 22m2 stops
from $622per person
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 typical for this route right now.

Flights to Wisconsin from Colorado Springs usually cost between $274 and $426 in October.
The lowest price found in the past 5 days was $285 on Delta (Oct 7-Oct 14).

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 December and October, when the average cost of round-trip tickets is $468 and $443 respectively.

Good to know

Low season

January

Cheapest flight

$147
Best time to beat the crowds but there is an average 6% increase in price.
Most popular time to fly with an average 26% increase in price.
Flight from Colorado Springs to Chicago O'Hare Airport

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: Minneapolis $304 one-way - $509 round-trip; Chicago $193 one-way - $364 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.
8.0
SouthwestOverall score based on 4195 reviews
8.6Crew
7.5Entertainment
7.0Food
8.1Boarding
8.0Comfort
Airline reviews

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.

8.0 ExcellentTamara, Aug 2026
Read more Southwest reviews

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.

Poor customer service, no accommodation for passengers when the flight was delayed over 5 hours.

The flight was late. The crew was rude. There was no food. Cramped and uncomfortable. Nothing about this flight was good.

It was great. The gate staff were very helpful in Portland when my son forgot his rolling bag and had to go back to get it just in time to make it on the plane. We really appreciate that. Great job!

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.

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

First flight was delayed which resulted in missing our connecting. As a result class was downgraded to economy on a later flight.

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.

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

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

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