ORD

$86 Find Cheap Flights from Florida Keys to Chicago - Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 21% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Flight Deals
Useful Info
Flight Deals

Cheap Flights from Florida Keys to O'Hare Intl

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Florida Keys to O'Hare Intl

Sat, Oct 31 - Wed, Nov 4
Frontier Logo
5:05 am - 6:16 pmMIA  Miami-ORD Chicago O'Hare Intl
14h 11m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
7:15 am - 9:31 pmORD  Chicago O'Hare Intl-MIA Miami
13h 16m1 stop Atlanta Hartsfield-Jackson
$175Frontier
Sat, Oct 31 - Mon, Nov 2
Frontier Logo
5:05 am - 12:51 pmMIA  Miami-ORD Chicago O'Hare Intl
8h 46m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
7:50 pm - 10:29 amORD  Chicago O'Hare Intl-MIA Miami
13h 39m1 stop Atlanta Hartsfield-Jackson
$176Frontier
Sat, Oct 24 - Mon, Oct 26
Frontier Logo
5:05 am - 11:32 amMIA  Miami-ORD Chicago O'Hare Intl
7h 27m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
10:26 am - 9:50 pmORD  Chicago O'Hare Intl-MIA Miami
10h 24m1 stop Atlanta Hartsfield-Jackson
$176Frontier
Wed, Oct 7 - Wed, Oct 14
American Airlines Logo
10:06 pm - 12:38 amMIA  Miami-ORD Chicago O'Hare Intl
3h 32mnonstop
American Airlines Logo
4:31 pm - 8:47 pmORD  Chicago O'Hare Intl-MIA Miami
3h 16mnonstop
$221American Airlines
Tue, Dec 29 - Tue, Jan 5
American Airlines Logo
5:05 am - 7:43 amMIA  Miami-ORD Chicago O'Hare Intl
3h 38mnonstop
American Airlines Logo
5:00 am - 9:15 amORD  Chicago O'Hare Intl-MIA Miami
3h 15mnonstop
$221American Airlines
Tue, Oct 20 - Tue, Oct 27
United Airlines Logo
12:26 pm - 2:55 pmMIA  Miami-ORD Chicago O'Hare Intl
3h 29mnonstop
United Airlines Logo
6:12 pm - 10:31 pmORD  Chicago O'Hare Intl-MIA Miami
3h 19mnonstop
$221United Airlines
Tue, Oct 27 - Wed, Oct 28
American Airlines Logo
5:15 am - 7:47 amMIA  Miami-ORD Chicago O'Hare Intl
3h 32mnonstop
American Airlines Logo
5:29 pm - 9:44 pmORD  Chicago O'Hare Intl-MIA Miami
3h 15mnonstop
$221American Airlines
Tue, Oct 27 - Wed, Oct 28
United Airlines Logo
8:45 am - 2:51 pmMIA  Miami-ORD Chicago O'Hare Intl
7h 06m1 stop Houston George Bush Intcntl
United Airlines Logo
10:43 am - 3:03 pmORD  Chicago O'Hare Intl-MIA Miami
3h 20mnonstop
$227United Airlines
Wed, Sep 30 - Wed, Oct 7
Delta Logo
12:03 pm - 6:45 pmMIA  Miami-ORD Chicago O'Hare Intl
7h 42m1 stop Atlanta Hartsfield-Jackson
Delta Logo
8:29 am - 5:46 pmORD  Chicago O'Hare Intl-MIA Miami
8h 17m1 stop Detroit Metropolitan Wayne County
$241Delta
Mon, Nov 23 - Tue, Dec 1
Delta Logo
8:00 am - 1:59 pmMIA  Miami-ORD Chicago O'Hare Intl
6h 59m1 stop Detroit Metropolitan Wayne County
Delta Logo
6:15 pm - 12:58 amORD  Chicago O'Hare Intl-MIA Miami
5h 43m1 stop Atlanta Hartsfield-Jackson
$241Delta
Useful Info

Good to know

Low season

January

Cheapest flight

$86
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly with an average 16% increase in price.
Flight from Miami to Chicago O'Hare Airport

FAQs for booking Florida Keys to Chicago flights

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

    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 Florida Keys to Chicago.

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

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

    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 Chicago with an airline and back to Florida Keys with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Florida Keys to Chicago?

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

Reviews of the top 3 airlines serving from Florida Keys to O'Hare Intl

 
Need help choosing which airline to fly with from Florida Keys to O'Hare Intl? 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.
7.4
United AirlinesOverall score based on 10213 reviews
7.1Entertainment
7.7Boarding
6.7Food
8.1Crew
7.3Comfort
Airline reviews

Kept changing the takeoff time and the moved it up so arrived when boarding had already started. Then sat waiting to taxi in for a long time

8.0 ExcellentMarlie, Sep 2026
Read more United Airlines reviews

Kept changing the takeoff time and the moved it up so arrived when boarding had already started. Then sat waiting to taxi in for a long time

Leaving at 7 when scheduled to leave at 4:20 - you tell me. Understood there was a ground stop. Then having to "reboot" the plane because of a lighting strike, also understood. But basically the flight was a "clusterf#$%".

Horrible experience. They delayed our flight 7 hours!! We had to seat at the airport with kids on 4th July all day!

Flights were on time. Free Wifi on plane. Everything was well organized.

Economy plus was so cramped I could not use my laptop. It was beyond bad.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

Flight was delayed two hours. No snacks and no tv screens. My bag got stuck in Chicago

Boarding was friendly and quick. While the plane model was older with no live tv, the entertainment was full of movies and tv shows. All food was available. Pilots were very communicative with status of the flight. Flight landed on time.

- flight was delayed several hours due to weather (understandable) - flight delayed further and we were told by attendants "we are not sure where the pilots are but they are on their way" as we have to find different pilots for the flight - announcements over the PA were somewhat unprofessional by the attendants, seems they need more training and were not reading off the script. They showed their young age and immaturity in their communications with the passengers. They were not clear and lacked professional communication language. - going from a hub to hub we were also parked at the tarmac at ohare for an additional hour and kept being told "few more minutes". Please just let the passengers know the real wait time instead of hiding the truth. We understand there is traffic and weather delays, but we just want transparency. There are several logistics of our lives that revolve around what the attendants and pilots are sharing with us but they are not being transparant.

Requested early boarding to disinfect seat, tray table, etc. before general boarding. Instructed to board after wheelchair passengers. Waited on jet bridge behind 12 wheelchair passengers. Stopped immediately after entering plane to wait for gate agent in rear of plane cleaning a seat that was wet, got to my row and found both seats adjacent to mine already occupied, with the lack of room making it impossible for me to clean my own space and defeating the purpose of my boarding early. Cleaned the armrests and tray table as best I could.

The new planes (American Eagle) are beautiful and especially comfortable. The flight attendants are consistently professional and courteous. And, while it may seem inconsequential, the new liquid tube of coffee creamer—in contrast to the powdered coffee creamer—makes all the difference in a cup of coffee.

Crew at the gate was very crabby and not at all polite. The plane was very hot the entire flight. And the seat cushion was very worn out.

The staff are very, very professional. It's what flying should feel like.

Waited for oxygen tanks for 30 minutes after boarding was complete.

Little warm on the plane and delayed for an hour

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

Lost bag and 2 days no word leaving for cruise no clothes or stuff

Food was ok, but not as good as I have had before on AA.

Flight was scheduled at 9:40pm. Got delayed to 10 am, the next day. crazy

The bag check, flight check-in, and onboard experience convinced my wife and me that we will actively go out of our way to avoid flying Frontier Airlines in the future. At bag check, we were informed that check-in could only be completed via the Frontier mobile app. Unfortunately, the app was extremely frustrating—sending us through repetitive, confusing loops that repeatedly forced us to decline add-on services with nearly every click. While most airline apps upsell, this one felt intentionally exhausting. As the process dragged on, we became genuinely concerned that my phone battery would die before check-in could be completed. We approached the bag check staff—who were standing together talking—and explained both our frustration and our predicament. They laughed. Later, my wife described the interaction as “gaslighting,” which felt accurate. We were then informed it would cost $25 per person simply to have our boarding passes printed. From that point forward, the tone of the experience was consistently hostile. The bag check employees were condescending and combative, behaving more like bullies than customer service staff. Unfortunately, that same attitude continued onboard. One flight attendant argued with me when I attempted to stow my backpack in the overhead bin. I explained that we had each paid $75 to check our bags specifically so we would not need to use carry-on space and could have adequate legroom. She demanded to see my ticket, pointed out that it said “no carry-on”—which I acknowledged—and I reiterated that this was precisely why we paid to check our bags. Her response was, “I don’t make the rules.” She then walked away, but not before asking if I “truly wanted to fly back to Chicago today?”—an unnecessary and unmistakable threat. It is also worth noting that despite booking our tickets together in the same transaction, we were not seated together. Upon our return to Chicago—where we could once again sit together—we compared onboard experiences. We both remarked on how unhappy the flight attendants appeared and how each of us was separately asked whether we would like to purchase a beverage. We declined. At no point was water mentioned as an option, leaving us with the clear impression that even water came at a cost—or that complimentary water, if available at all, was deliberately left unmentioned. Overall, the experience was shocking and deeply disappointing, but it was also a profound learning experience—one we will not forget and will not repeat. -Steve

Good for a budget airline! It was easy to get on, staff was really nice. Can’t say anything about the food or entertainment because it wasn’t available, which is fine.

This company socks. It's fraud. They canceled our flight yesterday, and today we were late because of a really long line at the check in bag. At the rebook station, there was ton of people. The workers were all rude. I am gonna make a report to FTC.

Too many extra fees, uncomfortable, little leg room. Will not recommend this airline.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

We were delayed three times ,and that destroyed my plans, and reservations

The crew was delayed because they came on another flight that was delayed due to weather 10pm flight left at 1.30 am The airline made no effort to align alternate crew

The flight itself was ok and the pilot was very communicative. However, our flight was delayed for almost 3 hours, the gate was changed 3 times and there was no communication as we were waiting. The flight staff was overall a little crabby...I understand as they probably had a long day but we all did.

Flying Frontier was a nightmare. From the booking through Kayak, checking in, departing and arriving, I will never recommend Kayak or Frontier.

Traveling to a place near O'Hare Intl?

Book flights to O'Hare Intl if you plan to visit one of these locations
Merrillville
Gurnee
South Haven
Oak Brook
Tinley Park
Hammond
Saint Joseph
Des Plaines
Elk Grove Village
Hoffman Estates
Portage
South Holland
Oakbrook Terrace
Willowbrook
Lansing
Alsip
Delavan
Lisle
Northbrook
Valparaiso

More options for your flight to O'Hare Intl