Find flights
When to book
FAQs & Tips
Airlines
Deals

Find cheap flights from Chicago to Kissimmee from $38

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 5/18. 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
0 bags
Tue 6/4
Tue 6/11

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

In the last 7 days travelers have searched 43,369,418 times on KAYAK, and here is why:

Save 22% 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.

Good to know

Low season

September

High season

March

Cheapest flight

$38
Best time to beat the crowds with an average 20% drop 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

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 41m.

  • How many flights are there between Chicago and Kissimmee?

    71 direct flights run between Chicago and Kissimmee on a daily basis. On average, there are about 502 departures each week.

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

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

  • 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 72 hours, the cheapest one-way ticket between Chicago and Kissimmee found on KAYAK was with Frontier for $38. Spirit Airlines offered a round-trip connection from $81 and Frontier from $83.

See more FAQs

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 11 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.
See more tips

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.
8.1
SouthwestOverall score based on 6092 reviews
7.3Food
8.1Comfort
7.8Entertainment
8.3Boarding
8.7Crew
Airline reviews

Landing was kinda fast and my ears were plugged for days after.

10.0 ExcellentMary, Apr 2024BNA - SRQ
Read more about Southwest reviews

Landing was kinda fast and my ears were plugged for days after.

Paid for early bird. Basically paid for nothing. Would have been in the same spot regardless since the entire plane family preboarded between A and B. If they can’t give you A they should be required to refund the early bird fee. Also I don’t know what the issue is with the flight attendants but their attitudes need to change.

Southwest is always good and effective. Would be nice if they raised the pre-boarding age a couple years. Would hate to have our 7 year old daughter sit by a complete stranger because of a goitch when i check in and get a late boarding number.

It was good. I wish you had gluten free snacks for my husband.

2 hour delayed departure, then sat on the tarmac for 30 minutes waiting for a gate in SRQ

As always it was a pleasure to fly on southwest.

Long layover in Chicago. Wish that could have been lessened.

Excellent! There was a delay due to the weather and they did all they could do to keep us comfortable & updated. Thank you!

Would have liked screens on the back of each seat.

With COVID still around, I wish they wouldn't bunch us up so much at the boarding gates.

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

The flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

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.

The control panel for the seat back screen did not work at all after takeoff.

Plane was so old it had cigarette butt trays in the seat

Everything was good, hard to really comfortable on a flight that long.

Good flights. Departure and arrivals were on time. DFW was a little problematic in that the Skytrain without prior notice bypassed the Echo terminal so that delayed my arrival at my connecting flight.

Because I can’t stand very long in one place, I was allowed to reword.

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Great flight. Boarding was efficient and quick. On time departure and smooth flight. Flight arrived early at destination. Good experience.

Had technical issue which delayed the flight period. Flight crew knew there was 5 passengers that the connecting flight was within 15 minutes once at the gate. Rather than identify the 5 passengers to assure they got first. The flight attended mentioned it but didn't assist to assure passengers with connecting flights off first. This caused a hardship and our party of 3 missed the connecting flight.

I don't like that I have to pay if I want extra leg room. The seats are so expensive; I sit in normal seats and my legs and knees cramp the entire flight. I never feel comfortable on AA flights.

Flight was delayed at departure due to weather and the need for de-icing. The flight was smooth but there was a delay at arrival due to weather. We were in a hold for 20 minutes or more. The flight arrived more than 30 minutes late. Airlines have no control over the weather and I'm glad that they follow all safety procedures. Had to wait a long time for my checked luggage. Whole process was slow and the bags arrived wet due to the rain. The onboard wifi and entertainment access was spotty and the signal was dropped several times. Otherwise the crew was great and friendly. They tried to get everyone's bags stowed and seated so we could take off.

Regarding the boarding: it needs more efforts to make it more convenient

Deicing in Denver took forever and I almost missed my connection. De-ice faster! Not Americans fault.

Everything was really good but the seats are not very comfortable.

Spirit canceled the flight in March and never notified me!

Pretty good. Would’ve been excellent if we would have left on time and the crew wasn’t late.

Spirit airline tries to screw you at every opportunity. Spirit wanted 65$ for an extra pound in the suitcase Made me open the suitcase at the counter to remove 1 pound. Staff very cold and rude Will never fly spirit again and will recommend same to family and friends

The weight limit per bag was really low - 40 lbs - so we had to pay extra. Then, they said their carry on size was 14x18x8, and we measured our bag very carefully. It was within the limit, yet they said it was too big, so we ended up paying an extra $100 for that too!! So it wasn’t the cheap flight we thought it would be. Then, they moved up our initial flight to depart 3 hours earlier which meant we had to be out on the road by 7 am and then have a 6 hour layover and we got home at 2am. It was a grueling day. I won’t be flying with them again.

Overall it was a good experience. Stewards were very kind and professional. The departure and arrival times were as promised. Plane was clean.

Terrible as usual!!!! Very unprofessional and rude flight attendants! You get what you pay for! HORRIBLE

My experience was above excellent!!!! First the lady that pushed me in the wheelchair to the gate was outstanding!!! Then the ladies at the gate went over and beyond, by helping me fill out the immigration form! I would not have been able to get to Guatemala without their help!!! God bless them all! They were amazing 🙏❤️🙏

First....my trip was from Ft. Myers to Philly (not the other way around). Plane was clean, staff was friendly and flight was efficient with boarding and flight time. Thumbs up all around.

Early departure and arrival. Cabin very cold. Waited a while for luggage to come out

Six hour delay. Poor customer service. No voucher. Bad communication. Missed important appointments.

I purchased a carry on bag online…was supposed to cost $72 but after a whole slew of bs charges, the total was over $175.00. Because of these hidden charges, I will not even consider flying Frontier ever again. It’s just not worth the hassle. I’m scratching this company off my list forever.

Flight delayed 3 times, resulting in late arrival, rental car place gave car away resulting in increased BS charges because I was late. Frontier blows.

It was impossible to change a carry-on for a checked bag after the initial selection. The flight was delayed 14 hours "to allow for a late arriving aircraft." The seats were shockingly uncomfortable. This was only the second time I've seen seats that didn't recline in an airline. The first was in an East Bloc airline before the fall if the Iron Curtain.

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.

First time flying Frontier, I am not sure the Ala Carte menu of options is for me.

I liked getting off the plane. Everything else was well below standards. Not even offering a bag of peanuts for free for a 4 hours flight is ridiculous.

There was no wifi, there was no usb charger on the planes Frontier lowered the weight limit on suitcases from 50 to 40 pounds Frontier now charges for a seat...really? If i don't pay for a basic seat, do i stand the whole flight? Frontier now charges for the carry on, just like for the checked suitcase The bundle pricing is way over priced.

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.

Bought seats on the flight and they were supposed to be 2 and a jumpseat. Plane clearly changed and it was a regular 3 seat row. Asked for a refund and was denied. If I wanted to sit next to someone else I wouldn't have bought the seats..

Book cheap flights from Chicago to Kissimmee

Recent round-trip flight deals

5/14Tue
1 stop
22h 55mORD-MCO
5/21Tue
nonstop
3h 09mMCO-ORD
$79
5/21Tue
nonstopSpirit Airlines
2h 49mORD-MCO
5/21Tue
1 stopSpirit Airlines
14h 08mMCO-ORD
$81
5/15Wed
nonstopFrontier
2h 56mORD-MCO
5/23Thu
nonstopFrontier
3h 09mMCO-ORD
$83
5/21Tue
nonstopFrontier
2h 58mORD-MCO
5/23Thu
nonstopFrontier
3h 09mMCO-ORD
$84
5/26Sun
1 stopSun Country Air
11h 42mORD-MCO
6/2Sun
1 stopSun Country Air
10h 03mMCO-ORD
$135
7/1Mon
1 stopSun Country Air
12h 49mORD-MCO
7/5Fri
1 stopSun Country Air
7h 39mMCO-ORD
$175
5/21Tue
1 stopDelta
5h 02mMDW-MCO
5/26Sun
1 stopDelta
5h 41mMCO-MDW
$202
5/21Tue
1 stopDelta
5h 02mMDW-MCO
5/22Wed
1 stopDelta
7h 10mMCO-MDW
$208
6/12Wed
1 stopSouthwest
8h 10mMDW-MCO
6/14Fri
1 stopSouthwest
10h 05mMCO-MDW
$281
6/12Wed
nonstopSouthwest
2h 30mMDW-MCO
6/14Fri
nonstopSouthwest
2h 45mMCO-MDW
$282

Search by stops

Search by airline

Search by price

Recent one-way flight deals

5/18Sat
nonstopFrontier
2h 58mORD-MCO
$38
5/18Sat
nonstopFrontier
2h 49mMDW-MCO
$38
5/28Tue
1 stopSpirit Airlines
26h 46mORD-MCO
$39
5/14Tue
1 stopSpirit Airlines
16h 49mORD-MCO
$40
5/15Wed
1 stopDelta
5h 48mMDW-MCO
$104
7/19Fri
1 stopDelta
4h 14mORD-MCO
$124
7/3Wed
1 stopAmerican Airlines
6h 44mORD-MCO
$128
6/22Sat
nonstopAmerican Airlines
2h 57mORD-MCO
$130
5/9Thu
nonstopUnited Airlines
2h 51mORD-MCO
$234
5/10Fri
2 stopsUnited Airlines
10h 47mORD-MCO
$273

Search by stops

Search by airline

Search by price

Last minute flights from Chicago to Kissimmee

Last minute flight, train and bus deals

5/7Tue
nonstop
2h 52mORD-MCO
5/14Tue
nonstop
3h 07mMCO-ORD
$98
5/7Tue
nonstop
2h 52mORD-MCO
5/14Tue
nonstop
3h 07mMCO-ORD
$105
5/10Fri
multi-stopFrontier
8h 25mMDW-MCO
5/22Wed
nonstopFrontier
2h 53mMCO-MDW
$110
5/8Wed
nonstop
2h 49mORD-MCO
5/15Wed
nonstop
3h 04mMCO-ORD
$112
5/9Thu
multi-stopFrontier
16h 15mORD-MCO
5/14Tue
nonstopFrontier
3h 07mMCO-ORD
$121
5/7Tue
nonstopSpirit Airlines
2h 53mORD-MCO
5/14Tue
multi-stopSpirit Airlines
14h 08mMCO-ORD
$130
5/8Wed
nonstopSpirit Airlines
2h 49mORD-MCO
5/15Wed
nonstopSpirit Airlines
3h 07mMCO-ORD
$141
5/10Fri
multi-stopDelta
4h 37mMDW-MCO
5/15Wed
multi-stopDelta
5h 41mMCO-MDW
$443
5/8Wed
multi-stopDelta
6h 44mMDW-MCO
5/15Wed
multi-stopDelta
5h 41mMCO-MDW
$508
5/8Wed
multi-stopPorter Airlines
10h 44mMDW-MCO
5/15Wed
multi-stopPorter Airlines
21h 02mMCO-MDW
$970

Search by stops

Search by airline

Search by price

Flights to Kissimmee

Browse origins: