$122 Find Cheap Flights from Colorado Springs to Wisconsin - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Colorado Springs to Wisconsin departing on 8/20. 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.
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Cheap Flights from Colorado Springs to Wisconsin

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Milwaukee
Milwaukee1 stop$265
Madison
Madison1 stop$309
Appleton
Appleton1 stop$315
Green Bay
Green Bay1 stop$329
Wausau
Wausau1 stop$475
Minneapolis
Minneapolisnonstop$309
Chicago
Chicagononstop$243
Duluth
Duluth1 stop$308
Milwaukee
Milwaukee1 stop$265
Madison
Madison1 stop$309
Appleton
Appleton1 stop$315
Green Bay
Green Bay1 stop$329
Wausau
Wausau1 stop$475
Minneapolis
Minneapolisnonstop$309
Chicago
Chicagononstop$243
Duluth
Duluth1 stop$308

Book Cheap Colorado Springs to Wisconsin Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Colorado Springs to Wisconsin 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 Colorado Springs to Wisconsin

Mon, Sep 14 - Wed, Sep 23
American Airlines Logo
5:01 am - 8:50 am
COS
-
ORD
2h 49mnonstop
American Airlines Logo
10:55 am - 12:48 pm
ORD
-
COS
2h 53mnonstop
$243American Airlines
Fri, Sep 11 - Mon, Sep 14
American Airlines Logo
12:37 pm - 4:30 pm
COS
-
ORD
2h 53mnonstop
American Airlines Logo
6:49 pm - 8:40 pm
ORD
-
COS
2h 51mnonstop
$248American Airlines
Tue, Aug 25 - Sat, Aug 29
United Airlines Logo
3:09 pm - 9:52 pm
COS
-
ORD
5h 43m
1 stop
United Airlines Logo
7:45 pm - 9:54 pm
ORD
-
COS
3h 09mnonstop
$253United Airlines
Fri, Sep 11 - Mon, Sep 14
American Airlines Logo
1:18 pm - 8:29 pm
COS
-
ORD
6h 11m
1 stop
American Airlines Logo
6:49 pm - 8:40 pm
ORD
-
COS
2h 51mnonstop
$258American Airlines
Tue, Aug 25 - Tue, Sep 8
American Airlines Logo
1:17 pm - 9:16 pm
COS
-
ORD
6h 59m
1 stop
American Airlines Logo
5:00 am - 9:18 am
ORD
-
COS
5h 18m
1 stop
$263American Airlines
Wed, Sep 9 - Fri, Sep 11
Delta Logo
1:25 pm - 8:56 pm
COS
-
ORD
6h 31m
1 stop
Delta Logo
1:51 pm - 7:56 pm
ORD
-
COS
7h 05m
1 stop
$273Delta
Tue, Aug 18 - Tue, Aug 25
Southwest Logo
1:15 pm - 9:25 pm
COS
-
MKE
7h 10m
1 stop
Southwest Logo
6:50 am - 12:35 pm
MKE
-
COS
6h 45m
1 stop
$275Southwest
Tue, Aug 25 - Sat, Aug 29
Delta Logo
8:10 am - 6:19 pm
COS
-
ORD
9h 09m
1 stop
Delta Logo
11:22 am - 9:38 pm
ORD
-
COS
11h 16m
2 stops
$278Delta
Thu, Aug 27 - Wed, Sep 2
Southwest Logo
11:20 am - 8:40 pm
COS
-
MKE
8h 20m
2 stops
Southwest Logo
6:20 am - 9:50 am
MKE
-
COS
4h 30m
1 stop
$285Southwest
Thu, Oct 22 - Mon, Oct 26
United Airlines Logo
11:57 am - 5:40 pm
COS
-
MKE
4h 43m
1 stop
United Airlines Logo
6:18 pm - 11:59 pm
MKE
-
COS
6h 41m
2 stops
$307United Airlines
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?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Colorado Springs to Wisconsin departing in September.

Flight prices are typical for this route right now.

Flights to Wisconsin from Colorado Springs usually cost between $212 and $371 in September.
The lowest price found in the past 5 days was $265 on American Airlines (Sep 1-Sep 9).

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Colorado Springs to Wisconsin, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

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 May and January, when the average cost of round-trip tickets is $424 and $408 respectively.

Good to know

Low season

January

Cheapest flight

$122
Best time to beat the crowds but there is an average 6% increase in price.
Most popular time to fly and prices are also 23% lower on average.
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 $328 one-way - $343 round-trip; Chicago $224 one-way - $432 round-trip

Reviews of the top 4 airlines serving from Colorado Springs to Wisconsin

 
See real verified KAYAK customer reviews for airlines flying from Colorado Springs to Wisconsin. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
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 4233 reviews
8.0Comfort
8.6Crew
7.0Food
7.5Entertainment
8.1Boarding
Airline reviews

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

2.0 MediocreIrene, Jun 2026
DEN - SFO
Read more Southwest reviews

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

This leg was much better, but we did have to have a 3 hour lay o er after coming from a very exhausting hiccup with our flight from BNA to Den

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!

My flight from Denver to Minneapolis was excellent. My flight from Minneapolis to Denver was one of the worst I flights I have ever experienced. I had a window seat, the gentleman in the middle seat was morbidly obese and SW should have made him purchase two seats. His elbow dug into my arm most of the way even after I asked to please be careful. I was literally squashed between the him and the window with no wiggle room. The plane was full so it was not possible to ask for a different seat. I realize I should have complained to the flight attendant but I didn't feel anything could be done to rectify the situation. I fly SW often, I will continue to do so as this was my first negative experience.

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.

Unprepared to rebook a flight of people. Uncommunicative. When I received updates in the app it was well after the announcement in the hold room. Offered a single $12 meal voucher, not enough for a sandwich at DEN, for a 17 hour delay. No one was able to explain their meal or hotel reimbursement policy for this cancellation, just handed a card to call the Help desk. My previous flight went through several delays and was finally cancelled, without explanation. The customer help desk closed while there was a long line. I then waited in line for a gate agent almost an hour while simultaneously on hold and trying to text with a remote Delta agent. Communicating with the text agent was almost impossible; they could not find any flights that got me back to my original city before the following evening. Kept offering itineraries that did not get me back to my origin airport or involved additional layovers. In 50 minutes on hold, never got through to an agent by phone. Finally spoke to one of the gate agents who was able to rebook on a red eye that had only one stop and got me back in the afternoon the next day, rather than late evening. Later by email, Delta offered 10,000 loyalty points for the inconvenience of the cancellation. The crew on the red eye flight were delightful. I don’t remember any food or entertainment on that flight.

I have Precheck. Flew HPN to DEN and return this past weekend. Delta didn't attach my Precheck number to this trip. So it was waiting in general line especially in Denver. Unavailable.

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.

Flight was late to take off Plane broke down Had to move everyone to another plane Told we weren’t going to LGA but Newark Also told we would be taken to NY But United lied and we ended up at Newark at 2 in the morning Horrible experience. And the experience of trying to get compensation from United is just as bad. They could not care less about their passengers Never again!

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.

The flight from Milwaukee to Dallas was great the staff absolutely amazing. After that EVERYTHING WENT DOWN HILL!!! ABSOLUTELY HORRIBLE!!! WILL NOT FLY THIS AIRLINE AGAIN

not sure why you ask about food, I n3ver get food on flights except maybe cookies or pretzels. wifi was slow and in and out most of the flight not good.

there are no options s for snack besides cookies would ve nice to have a salty option n

Never ontime and always delays. Long waits for customer service and often app doesn’t work

We were upgraded to First Class and it was a great flight

it was fine, decent flight... dont get food besides cookies or pretzels so not sure why you ask about food. same for entertainment..

this plane was really old, had exit row seats and tray was in arm of seat so super uncomfortable to use. another seat they could t even use the tray it was broke. seat i. front of me had duct tape on it cause seat was ripped open... this plane should either be updated or retired.

We loved the steward on the plane. He made the night enjoyable

American airlines suck they delay the flights all the time made me sleep in an airport because my flight was delayed and I miss my connecting flight

Very poor delay in dfw was really bad n long

Everything you need to know for your flight from Colorado Springs to Wisconsin

Information on your arrival and departure airports