$91 Find Cheap Flights from Chicago to Key Largo - 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 Key Largo departing on 8/27. 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

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Everything you should know

Cheapest round-trip
$177
Typical prices: $168-$367
United Airlines
Wed 10/14Wed 10/28
ORD - MIA • Non-stop
Cheapest non-stop
$181
Typical prices: $168-$375
United Airlines
Fri 10/30Mon 11/2
ORD - MIA • Non-stop
Arrival airport
You can't fly directly to Key Largo. It is served by Miami (MIA), located 49.7 miles from Key Largo.
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Flight Deals
Useful Info
Flight Deals

Cheap Flights from Chicago to Key Largo (CHI-MIA)

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

Wed, Oct 14 - Wed, Oct 28
United Airlines Logo
7:30 am - 11:55 am
ORD
-
MIA
3h 25mnonstop
United Airlines Logo
5:34 pm - 11:49 pm
MIA
-
ORD
7h 15m
1 stop
$177United Airlines
Tue, Sep 1 - Tue, Sep 8
United Airlines Logo
6:00 am - 2:46 pm
ORD
-
MIA
7h 46m
1 stop
United Airlines Logo
12:17 pm - 2:48 pm
MIA
-
ORD
3h 31mnonstop
$177United Airlines
Sat, Oct 3 - Sat, Oct 10
Frontier Logo
1:06 pm - 10:00 pm
MDW
-
MIA
7h 54m
1 stop
Frontier Logo
6:00 am - 12:07 pm
MIA
-
MDW
7h 07m
1 stop
$177Frontier
Wed, Aug 26 - Sat, Aug 29
Southwest Logo
9:25 am - 1:25 pm
MDW
-
MIA
3h 00mnonstop
Southwest Logo
6:30 am - 10:40 am
MIA
-
MDW
5h 10m
1 stop
$177Southwest
Thu, Aug 20 - Mon, Aug 24
Frontier Logo
7:30 am - 11:54 am
ORD
-
MIA
3h 24mnonstop
Frontier Logo
8:10 am - 7:59 pm
MIA
-
ORD
12h 49m
1 stop
$178Frontier
Fri, Sep 11 - Mon, Sep 14
American Airlines Logo
4:35 pm - 8:55 pm
ORD
-
MIA
3h 20mnonstop
American Airlines Logo
6:55 am - 9:29 am
MIA
-
ORD
3h 34mnonstop
$181American Airlines
Sat, Sep 5 - Tue, Sep 8
American Airlines Logo
4:10 pm - 8:28 pm
ORD
-
MIA
3h 18mnonstop
American Airlines Logo
8:00 pm - 10:31 pm
MIA
-
ORD
3h 31mnonstop
$181American Airlines
Mon, Oct 26 - Thu, Oct 29
Southwest Logo
3:45 pm - 11:05 pm
MDW
-
MIA
6h 20m
1 stop
Southwest Logo
6:40 am - 8:45 am
MIA
-
MDW
3h 05mnonstop
$181Southwest
Mon, Sep 14 - Wed, Sep 16
Multiple Airlines Logo
12:54 pm - 10:17 pm
MDW
-
MIA
8h 23m
1 stop
Multiple Airlines Logo
6:25 pm - 10:44 pm
MIA
-
MDW
5h 19m
1 stop
$194Multiple Airlines
Thu, Oct 1 - Sat, Oct 3
Multiple Airlines Logo
1:01 pm - 10:00 pm
ORD
-
MIA
7h 59m
1 stop
Multiple Airlines Logo
12:10 pm - 4:33 pm
MIA
-
ORD
29h 23m
1 stop
$285Multiple Airlines
Useful Info

Good to know

Low season

September

Cheapest flight

$91
Best time to beat the crowds with an average 21% drop in price.
Most popular time to fly with an average 5% increase in price.
Flight from Chicago Midway Airport to Miami

When to book flights from Chicago to Key Largo

Are your dates flexible? Find out the best times to travel from Chicago to Key Largo 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 Key Largo

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

    When flying out of Chicago you’ll be using one of these airports: Chicago Midway, Chicago O'Hare Intl or Chicago Greater Rockford. Key Largo does not have its own airport so you’ll be flying into nearby Miami airport, which is 49.7 mi away.

  • How long does a flight from Chicago to Key Largo take?

    Direct flights cover the 1,186 miles separating Chicago and Key Largo in about 3h 00m.

  • How many flights are there between Chicago and Key Largo?

    62 direct flights run between Chicago and Key Largo on a daily basis. On average, there are about 440 departures each week.

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

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

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

    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 Key Largo.

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

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

    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 Key Largo 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 Key Largo?

    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 Key Largo 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 Key Largo?

    In the last 5 days, the cheapest one-way ticket between Chicago and Key Largo found on KAYAK was with Frontier for $32. Frontier offered a round-trip connection from $57 and JetBlue from $89.

Top tips for finding cheap flights from Chicago to Key Largo

  • There is no airport in Key Largo. Instead, you’ll be flying into Miami Airport when flying between Chicago and Key Largo.
  • The cheapest flight from Chicago to Key Largo was found 65 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 June, July and August. The cheapest month to fly is January.

Reviews of the top 5 airlines serving Chicago to Key Largo

 
Need help choosing which airline to fly with from Chicago to Key Largo? 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 4221 reviews
7.0Food
8.0Comfort
7.5Entertainment
8.1Boarding
8.6Crew
Airline reviews

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

10.0 ExcellentDenis, Aug 2026
MDW - ATL
Read more Southwest reviews

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

Overall good, just screaming kids in the area the whole flight.

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

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

Excellent experience. WiFi worked on this leg of My trip

It was hot and not as comfortable as the flight to Chicago. Must have been a different plane that needs to be worked on or replaced.

The SFO lounge closes at 12 midnight. My flight took off at 2AM

It was extremely hot in the cabin the entire flight, vent air was worn

Have not had a flight out or returning to Norfolk that has not required maintenance, and a gate delay. Properly staff the crew so maintenance can be performed without last minute emergencies on each flight and there is enough staff to have gates prepared for inbound flights. Staff to ensure the safety and on time service vs. profit.

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.

I liked the entertainment on JetBlue, the service from JFK to JAX was terrible at best

I usually dont fly JeTBlue and I dont think I will ever do it again. The flight was delayed fee time, nobody was giving us any info at at the airport, gate changing, the slowest and poorly organized boarding ever, rude staff.. huh

Like the variety of entertainment options. One crew member was a little on the rough/rude side. Boarding was a mess, attendants didn't do a great job of helping with the luggage storage and it delayed us a couple of minutes.

Flight is delayed by more than an hour without any reason, the jet blue gates kept changing every 20 mins and there is no proper communication. No ear phones provided in flight, there is a screen with entertainment but what is the use, I have earphones but the console has outdated audio connections, no usb C or bluetooth, they are living 15 years behind

Flight was cancelled, no support at JFK even though it is their main hub.. wait times on the phone was very long

I liked the punctuality, the crew, and overall the whole flight

When I agreed to give up my two seats because of overbooking by the airline, I should have been offered some sort of reward or credit towards a future flight. I was not. It was not until the next day when I mentioned it to a Jet Blue employee that I was advised to call 1-800-JetBlue. So here I am, having done Jet Blue a favor and I had to do the work to find out if I was going to get a credit. Such service

It's not JetBlues fault but there was a smell on the plane (possibly other travelers) and 3 children behind me that never quit whining. Soccor fans that were very loud. Pilot brought the plane down from high altitude quickly, dropping us hu dress of feet at a time. I've never felt that intense of dropping on other airlines (usually fly Southwest Airlines). But I arrived safely and I'm thankful for that.

Seats were great, the staff was great, and the food was about the best I've had on a plane, and is especially the best of any US-based carrier I've flown. Free Wi-Fi was also great.

The aircraft was fine, it’s was just the service. The flight got canceled several times and that was very inconvenient for my 69 years old mom.

I had my flight of Cedar Rapids. THen Chicago to Boston. Flight out of Cedar rapids was delayed by 12 hrs. Had to drive to Chicago to catch my flight

Long delays to board due to mechanical issues with plane.

Flight was delayed, boarded, sat at the gate for more than 30 minutes, left the gate then waited on the pad for another 30 to 60 minutes then returned to the gate, deboarded and was cancelled... alternative flight was not booked automatically. Waited in line for 30 minutes but fortunately an alternate flight to a different destination was found ... no thanks to the travel agent used by kayak

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

I was very unhappy with the lack of communication from the cockpit. It took close to a half an hour before we took off after the doors were closed, and we got no announcements as to progress. It would be nice to get some acknowledgement of the situation and updates as to when we are taking off.

The flight was delayed significantly. Communication during the flight was abrupt and caused some panic as we were navigating turbulence. It was also too loud and every announcement felt startling. The flight attendants did not offer any assurances and I felt unsettled most of the flight. The seats, floor and tray table was very dirty. The seat next to me was broken and the passenger sitting there was very uncomfortable. He had a spring in his back and his seat made terrible squeaking noises through the flight.

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 Key Largo

Complete your trip to Key Largo with a hotel stay or car rental