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Find cheap flights from Chicago to Florida from $28

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 Florida departing on 5/28. 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
Sun 6/9
Sun 6/16

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Best Florida Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Orlando
Orlandononstop$57
Miami
Miaminonstop$37
Fort Lauderdale
Fort Lauderdalenonstop$77
Tampa
Tampanonstop$59
Fort Myers
Fort Myersnonstop$62
Jacksonville
Jacksonville1 stop$140
Sarasota
Sarasota1 stop$150
Pensacola
Pensacola1 stop$95
Key West
Key West1 stop$248
Panama City
Panama City2 stops$302
Valparaiso
Valparaisononstop$130
Punta Gorda
Punta Gordanonstop$129
Tallahassee
Tallahassee1 stop$328
Gainesville
Gainesville1 stop$332

Good to know

Low season

September

High season

March

Cheapest flight

$28
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly with an average 29% increase in price.
Flight from Chicago O'Hare Airport to Fort Lauderdale

FAQs - booking Florida flights

  • Are pet/service animal relief areas at Tampa International Airport (TPA)?

    The airport has several designated areas for pets and service animals to use for relieving themselves. In the grassy area across the vehicle drives of the departure and arrival area is an outdoor pet relief area. The other pet relief areas are past the security at the gate level on each airside building; the areas have receptacles, drinking sinks, and disposable waste bags.

  • Are there kids-friendly amenities at Chicago O’Hare International Airport (ORD)?

    Yes. ORD provides nursing stations for mothers to pump or feed their kids. The nursing facilities are on Terminal 1, concourse B by Gate B10, Terminal 2, concourse F next to the Crossover between Gates E9 and E5, Terminal 3, concourse L by Gate L6, and Terminal 5, concourse M next to Gate M20. Additionally, ORD has nursing pods on Terminal 1 on concourse B by Gate B7, concourse C by Gates C11 and C23, and on Terminal 2, on concourse E close to Gate E1. On Terminal 2, in the main hall close to Gate F1, a Family Lounge offers a delegated space for kids to play.

  • Is there a rental car center at Tampa International Airport (TPA)?

    TPA has several rental car companies on its premises. To reach TPA’s onsite rental car center you’ll take the SkyConnect Train from the Main Terminal. SIXT, Payless, Alamo, Budget, Avis, National, Enterprise, Hertz, and Dollar are some of the onsite rental car agencies. Moreover, TPA has an off-airport rental car faculty, which is at one's disposal at the end of Blue and Red Luggage Claim via service courtesy vehicle.

  • Are there airline lounges at Chicago O'Hare International Airport (ORD)?

    The United Lounge is on Terminal 1 close to Gates B6, B18, and C16, and Terminal 2 is next to Gate F9. The Admiral’s Club is on Terminal 3 next to Gates G8, L2A, and H6/K6. On Terminal 5, there is the Sky Club next to Gate M13, SAS Lounge next to Gate M19, Swissport Lounge close to Gate M13, and British Airways Lounge close to Gate M17. The United Polaris Lunges is in Terminal 1 near Gate C18. Passengers who don't own membership to the airline clubs in ORD can purchase a day's pass for most of the airline lounges.

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

    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 Florida.

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

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

    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 Florida 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 Florida?

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

See more FAQs

Top tips for finding cheap flights to Florida

  • Morning departure is around 12% more expensive than an evening flight, on average*.
  • Chicago International Airport (ORD) is one of the main airports serving the city of Chicago. ORD is a hub for United Airlines and American Airlines both facilitating flights from Chicago to Florida.
  • If you’re looking to unwind and revitalize before your flight to Florida, check out the yoga room in ORD. The yoga room provides complimentary yoga mats as well as a place to stow your belongings. The yoga room is situated in Terminal 3, on the Mezzanine Level, open daily from around 6 am to 10 pm.
  • If you need a place to rest after your flight from Chicago, Orlando International Airport (MCO) has a hotel. The Hyatt Regency Hotel is situated between Terminals A and B.
  • Miami International Airport (MIA) is one of the airports serving the metropolis of Miami and is a hub for American Airlines, which facilitates flights to Florida from Chicago.
  • MIA has a multi-sensory room offering passengers with hidden disabilities a spot to de-stress after their flight. The sensory room is on concourse D adjacent to the TSA security checkpoint 4.
See more tips
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

Top 5 airlines serving from Chicago to Florida

 
Need help choosing which airline to fly with from Chicago to Florida? 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.
8.3
EVA AirOverall score based on 1524 reviews
7.9Food
8.4Boarding
8.2Comfort
8.6Crew
8.0Entertainment
Airline reviews

The type of the food requested (Asian vegetarian) was not properly met with. They have very limited snack items that may compensate for the main meals.

8.0 ExcellentAnonymous, Apr 2024TPE - JFK
Read more about EVA Air reviews

The type of the food requested (Asian vegetarian) was not properly met with. They have very limited snack items that may compensate for the main meals.

The quality of the food is pretty good. Thank you, EVA Air.

Fast and efficient boarding. Flight was on time. Service was very good for our long flight. First time flying with this airline and I would highly recommend.

Eva Air's Business Class is pretty decent. With the given price, I think that the food can be better.

Pleasant crew. Very long flight, a bit uncomfortable at times being seated, but not too bad.

No ice for the drinks. Only gave a half a cup of your beverage. Not enough water. I got very dehydrated.

Eva air is a good airline. The seats on the way to Taipei could have certainly been more comfortable, but all in all it was a pretty good experience.

Eva is one of the top airlines in Asia... but often are over priced. Finally found a reasonable rate.

My original flight was rescheduled & EVA did a good job rescheduling my flight & connecting flight.

Polite hard working crew. No complaints really. Meals were not to my liking.

I’ve had a couple flights this week on United that were delayed by an hour or more

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

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.

Terrible… missed our flight due to ridiculously long time to go thru baggage check-in!

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.

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 Florida

Recent round-trip flight deals

5/22Wed
nonstopFrontier
3h 11mMDW-MIA
5/29Wed
nonstopFrontier
3h 15mMIA-MDW
$37
5/29Wed
nonstopSpirit Airlines
3h 19mORD-MIA
6/5Wed
nonstopSpirit Airlines
3h 26mMIA-ORD
$39
5/21Tue
nonstopSpirit Airlines
3h 17mORD-MIA
5/22Wed
nonstopSpirit Airlines
3h 25mMIA-ORD
$40
5/26Sun
nonstopUnited Airlines
3h 02mORD-RSW
5/29Wed
nonstopUnited Airlines
3h 17mRSW-ORD
$169
5/26Sun
nonstopAmerican Airlines
2h 54mORD-PBI
5/31Fri
nonstopAmerican Airlines
3h 17mPBI-ORD
$189
8/14Wed
1 stopDelta
6h 01mORD-MCO
8/24Sat
1 stopDelta
6h 54mMCO-ORD
$196
8/6Tue
nonstopAmerican Airlines
2h 34mORD-TPA
8/12Mon
nonstopAmerican Airlines
3h 02mTPA-ORD
$197
8/13Tue
1 stopDelta
6h 01mORD-RSW
8/20Tue
1 stopDelta
7h 14mRSW-ORD
$216
8/3Sat
nonstopUnited Airlines
2h 31mORD-JAX
8/10Sat
nonstopUnited Airlines
2h 43mJAX-ORD
$323
6/1Sat
1 stopJetBlue
10h 17mORD-PBI
6/3Mon
1 stopJetBlue
6h 55mPBI-ORD
$451

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Recent one-way flight deals

5/28Tue
nonstopSpirit Airlines
3h 06mORD-FLL
$28
6/3Mon
nonstopSpirit Airlines
3h 07mORD-FLL
$29
6/12Wed
nonstopFrontier
3h 07mMDW-MIA
$29
5/29Wed
nonstopFrontier
2h 48mMDW-MCO
$29
8/7Wed
nonstopUnited Airlines
3h 02mORD-RSW
$89
6/5Wed
nonstopAmerican Airlines
2h 45mORD-TPA
$89
5/16Thu
nonstopAmerican Airlines
2h 52mORD-RSW
$95
8/7Wed
1 stopDelta
5h 53mORD-MCO
$98
7/9Tue
1 stopDelta
4h 30mMDW-MCO
$98
8/10Sat
nonstopUnited Airlines
3h 10mORD-FLL
$135

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Last minute flights from Chicago to Florida

Last minute flight, train and bus deals

5/15Wed
multi-stopSpirit Airlines
7h 57mORD-FLL
5/21Tue
nonstopSpirit Airlines
3h 10mFLL-ORD
$70
5/14Tue
multi-stop
7h 02mORD-MCO
5/15Wed
nonstop
3h 04mMCO-ORD
$87
5/15Wed
nonstopFrontier
3h 17mMDW-MIA
5/16Thu
multi-stopFrontier
5h 11mMIA-MDW
$95
5/15Wed
nonstopFrontier
3h 17mMDW-MIA
5/17Fri
multi-stopFrontier
9h 32mMIA-MDW
$99
5/15Wed
multi-stopDelta
7h 31mORD-RSW
5/22Wed
multi-stopDelta
8h 44mRSW-ORD
$216
5/15Wed
multi-stopDelta
6h 45mMDW-MIA
5/22Wed
multi-stopDelta
5h 35mMIA-MDW
$216
5/11Sat
nonstopAmerican Airlines
2h 38mORD-MCO
5/14Tue
nonstopAmerican Airlines
3h 01mMCO-ORD
$243
5/14Tue
nonstopAmerican Airlines
2h 48mORD-RSW
5/18Sat
nonstopAmerican Airlines
3h 11mRSW-ORD
$313
5/11Sat
nonstopUnited Airlines
2h 47mORD-TPA
5/15Wed
nonstopUnited Airlines
3h 05mTPA-ORD
$363
5/15Wed
nonstopUnited Airlines
3h 03mORD-RSW
5/17Fri
nonstopUnited Airlines
3h 15mRSW-ORD
$377

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Flights to Florida

Return flight deals:

Florida - Chicago

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$409
$728
$420
$43

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