$87 Find Cheap Flights from Chicago to Kissimmee - 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 Chicago to Kissimmee departing on 7/4. 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

KAYAK searches hundreds of travel sites at once for deals on flights from Chicago to Kissimmee

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Free to useThere are no hidden charges or fees.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$175
Typical prices: $137-$337
Frontier
Tue 9/15Sat 9/26
ORD - MCO • Non-stop
Cheapest non-stop
$175
Typical prices: $199-$420
Frontier
Sat 7/25Wed 7/29
ORD - MCO • Non-stop
Arrival airport
You can't fly directly to Kissimmee. It is served by Orlando (MCO), located 11 miles from Kissimmee.
FAQs
FAQs
FAQs
FAQs
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Kissimmee!
Flight Deals
Useful Info
Flight Deals

Cheap Flights from Chicago to Kissimmee (CHI-MCO)

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

Tue, Sep 15 - Sat, Sep 26
Frontier Logo
4:49 pm - 8:42 pm
ORD
-
MCO
2h 53mnonstop
Frontier Logo
7:10 am - 12:02 pm
MCO
-
ORD
5h 52m
1 stop
$175Frontier
Sat, Oct 3 - Sat, Oct 10
Frontier Logo
4:49 pm - 8:42 pm
ORD
-
MCO
2h 53mnonstop
Frontier Logo
10:58 am - 1:16 pm
MCO
-
ORD
3h 18mnonstop
$176Frontier
Tue, Aug 4 - Sat, Aug 8
Frontier Logo
5:13 pm - 9:25 pm
ORD
-
MCO
3h 12mnonstop
Frontier Logo
8:59 pm - 11:10 pm
MCO
-
ORD
3h 11mnonstop
$177Frontier
Wed, Jul 15 - Sat, Jul 18
Frontier Logo
5:13 pm - 9:25 pm
ORD
-
MCO
3h 12mnonstop
Frontier Logo
8:59 pm - 11:10 pm
MCO
-
ORD
3h 11mnonstop
$178Frontier
Wed, Aug 19 - Sat, Aug 22
Frontier Logo
7:44 pm - 11:29 pm
ORD
-
MCO
2h 45mnonstop
Frontier Logo
9:00 pm - 11:08 pm
MCO
-
ORD
3h 08mnonstop
$179Frontier
Tue, Aug 4 - Sat, Aug 8
Frontier Logo
5:13 pm - 9:25 pm
ORD
-
MCO
3h 12mnonstop
Frontier Logo
8:59 pm - 11:10 pm
MCO
-
ORD
3h 11mnonstop
$180Frontier
Mon, Aug 10 - Tue, Aug 18
Frontier Logo
10:16 am - 2:23 pm
ORD
-
MCO
3h 07mnonstop
Frontier Logo
9:30 am - 4:00 pm
MCO
-
ORD
7h 30m
1 stop
$181Frontier
Thu, Aug 6 - Tue, Aug 11
Frontier Logo
5:13 pm - 9:25 pm
ORD
-
MCO
3h 12mnonstop
Frontier Logo
1:07 pm - 8:52 pm
MCO
-
ORD
8h 45m
1 stop
$182Frontier
Thu, Oct 8 - Sun, Oct 11
Frontier Logo
4:49 pm - 8:42 pm
ORD
-
MCO
2h 53mnonstop
Frontier Logo
3:42 pm - 8:28 pm
MCO
-
ORD
5h 46m
1 stop
$183Frontier
Tue, Aug 4 - Thu, Aug 6
Frontier Logo
9:28 am - 12:05 am
ORD
-
MCO
13h 37m
1 stop
Frontier Logo
8:59 pm - 11:10 pm
MCO
-
ORD
3h 11mnonstop
$184Frontier
Useful Info

Good to know

Low seasonApril
Cheapest flight$87
Best time to beat the crowds but there is an average 4% increase in price.
Most popular time to fly with an average 31% increase in price.
Flight from Chicago O'Hare Airport to Orlando Airport

When to book flights from Chicago to Kissimmee

Are your dates flexible? Find out the best times to travel from Chicago to Kissimmee based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Flights from Chicago to Kissimmee: the best tips from KAYAK users' own experiences

Insights shared by verified travelers who flew the route from Chicago to Kissimmee 
SteveFlew with Spirit Airlines
ORD
-
MCO
Mar 2026
Bring a seat cushion if you're flying Spirit.
LaurenFlew with Spirit Airlines
ORD
-
MCO
Feb 2024
If you can get by with a personal item, spirit has the best prices often at the best times to fly chicago to orlando for a weekend

FAQs for booking flights from Chicago to Kissimmee

  • Which airports will I be using when flying from Chicago to Kissimmee?

    When flying out of Chicago you’ll be using one of these airports: Chicago Midway, Chicago O'Hare Intl or Chicago Greater Rockford. Kissimmee does not have its own airport so you’ll be flying into nearby Orlando airport, which is 11.0 mi away.

  • How long does a flight from Chicago to Kissimmee take?

    Direct flights cover the 994 miles separating Chicago and Kissimmee in about 2h 30m.

  • How many flights are there between Chicago and Kissimmee?

    76 direct flights run between Chicago and Kissimmee on a daily basis. On average, there are about 535 departures each week.

  • What’s the cheapest day of the week to fly between Chicago and Kissimmee?

    Consider leaving on a Friday and avoid Mondays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Thursdays and the most expensive ones on Mondays.

  • How does KAYAK find such low prices on flights from Chicago to Kissimmee?

    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 Kissimmee.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Kissimmee 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 Kissimmee?

    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 Kissimmee 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 Kissimmee?

    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 Kissimmee from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • Which airlines provide the cheapest flights from Chicago to Kissimmee?

    In the last 5 days, the cheapest one-way ticket between Chicago and Kissimmee found on KAYAK was with Frontier for $34. Frontier offered a round-trip connection from $64 and Allegiant Air from $156.

Top tips for finding cheap flights from Chicago to Kissimmee

  • There is no airport in Kissimmee. Instead, you’ll be flying into Orlando Airport when flying between Chicago and Kissimmee.
  • The cheapest flight from Chicago to Kissimmee was found 62 days before departure, on average.
  • Book at least 1 week before departure in order to get a below-average price.
  • High season is considered to be February, March and April. The cheapest month to fly is January.

Reviews of the top 5 airlines serving Chicago to Kissimmee

 
Need help choosing which airline to fly with from Chicago to Kissimmee? 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 4245 reviews
7.0Food
8.0Comfort
7.5Entertainment
8.6Crew
8.1Boarding
Airline reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

6.0 GoodAnonymous, Jun 2026
MDW - BDL
Read more Southwest reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

Excellent experience. WiFi worked on this leg of My trip

The crew was very inconsiderate and rude. My flight was scheduled to depart at 6:00am. I received a call from the crew at 5:40am, asking if I was going to make the flight because I was the only one that hasn't boarded yet and boarding ends at 5:50am. I let them know that I will be at the gate in a few minutes, before the 5:50am cutoff. When I arrived at the gate at 5:45am the gate was closed. Departing early on last minute notice without having all passengers on board is inconsiderate and unprofessional.

Very easy to use and convenient, you can perform any action within the same portal

Okay considering we had weather delays which the Pilot notified us of immediately!

The boarding was organized and informative but the plane was tight meaning that you were sitting on one another and extremely uncomfortable. It’s disappointing that can’t have common seating comfort on the plane.

Everything could have benn better. Short fly, no food, no entertainment and no wifi.

Stop changing gates. Stop cancelling flights Stop moving my seat.

The staff was frielndly. The plane was terrible, it was too small and should be decommissioned. There were no back seat screens at all. The only beverages we had a choice from was coffee, tea or water. The only bathroom in the back was behind the flight attendant's jump seat and wasn't working. And I literally felt like I was sitting on top of the guy next to me. It was terribly hot in the plane and we had to sit on the tarmac in Chicago for 1/2 hour due to congestion in Mpls. Wouldn't they have know that before they even boarded us so that we could have sat in comfort in the terminal?

This was one of the worst flights I’ve been on in years. I upgraded to comfort and had such an uncomfortable experience. The person next to me was oversized - which I understand - however, they took up their space and mine. I could only use about 50% of my seat space to not be physically touching this person the entire flight and there was no spatial awareness. I also could not use the seat outlet because their body was obstructing it. It was very inconvenient. Their body kept touching me repeatedly during the flight and I felt very uncomfortable. To pay more for an upgraded space and then not even being able to use it was highly disappointing.

It was very cold because the air conditioner was on high power, and my son got sick.

The boarding process was terrible especially with an indirect flight Chicago to Seattle to San Diego was terrible talking about we overbooked a flight idk if I’d take this airline ever again we got off our flight from Chicago to Seattle and we traveled for business and they told us our connecting flight was over booked and their was no seats asking people to take a delayed next flight and they don’t tell anyone coughing to wear masks seats 30A-B were terrible during the flight no one wants to sit next to people coughing all around I don’t want to be sick traveling for work or get sick anytime it’s very upsetting the staff doesn’t take this stuff serious to tell them to wear masks when they see people coughing and sneezing

Great experience. Boarding was fast, staff were very nice and funny, everything at the seat worked well.

Horrible! Several delays and then was cancelled! I spent over 24 hours in the airport and was unable to get a hotel or food voucher.

Boarded early; and arrived home 40 mins early. After a long flight, it’s nice to be back home early. These flights have no amenities; no snacks. So need to bring your own

A long delay. Don't travel late in the day.

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

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.

Always wish for more healthy, gluten free options. We have to bring our own.

Our seats were all the way in back of the plane,

The flight attendants in First Class were mediocre at best. They did not take our tray away until we were about to land and only did so when I press the call button. The United person at the United Club was asked to get us our boarding pass since we missed the flight due in Chicago. She argued that we did not have seats on the flight given to us in Moline. Furthermore, she was adamant that we did not have a First Class ticket. After I spent much time with her trying to show we were correct, she reluctantly agreed. She was probably the most incompetent ticketing person I have ever met and I have traveled 3 million miles on United plus many additional miles with other carriers. United has definitely deteriorated in more than on way.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

Significant delays on my trip to Chicago and my trip back to NY

Delayed by 5 hours and I had to wit in the airport for more than 6+ hours.

I’ve got 31F seat and window seat . My 2 co passengers was AA crew members and they were very rude attitude and when I was going to use bathroom their gestures was very different and awkward and the guy beside me completely occupied the hand rest and I was really uncomfortable

It was so much better than expected, Ohare is not such a pleasant experience but American Airlines with the new, clean aeroplane and free Wi-Fi was outstanding and the crew so pleasant and helpful.

It wa sort of on time; the cab was left with some trash

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.

The Airline was not prepared for weather delays. We were held up due to an incoming flight being delayed and so we did not have a flight crew. This caused an extra delay for departure by 2 hours.

From the moment I walked into the airport in Chicago to the moment I was walking off the plane in Florida I had an unforgettable experience! I was traveling with my 3 month old by myself and everyone just made sure I was taken care of. I couldn’t thank them enough!

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

Better than expected. Staff were friendly and nice on both flights.

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

Our flight was canceled for no known reason. We weren’t told until we were checking in at 5:00 am. This was after our last flight with Frontier where we sat on the plane for three hours (not an exaggeration) before we took off because of a mechanical issue. We won’t be flying Frontier again.

I didn’t have enough time to catch my connecting flight and had to use a different Airline. I will be requesting a refund.

I brought a ticket and car rental through Travelocity. There was no where to add a KTN. So I thought i’d add it by looking up ticket on frontier website. I tried 3 times with the frontier chat bot to add my KTN it never updated my boarding pass. So then I tried showing up early to do it in person at the airport. The first employee update my ktn in the system and gave me a new boarding pass. I was sent back by tsa to join regular line. Then I was told to add my Ktn. It would cost me $25 extra. Given the length of the cue I did pay. Congratulations! BUT I will NEVER fly frontier again. Plus the plane was very old. It had actual ashtrays and old looking tray backs. Worst travel experience ever. Im warning my friends and family not to use frontier ever.

It was delayed 9 hours for operational reasons, despite the plane arriving to the airport on time.

Was just ok with over selling I guess. A lot of people in a short space and when we finally arrive i20 minutes, waiting to get out from the plain because we were waiting authorization for out boarding? Something like that.

They changed my flight and did not want to accommodate me or try to help me in any way. They do not care about their customers.

Everything you need to know for your flight from Chicago to Kissimmee

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