HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Illinois

$60+ Cheap flights from Florida Keys to Illinois

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/10. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — ORD
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Florida Keys to Illinois with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Florida Keys to Illinois

Cheapest flights from Florida Keys to Illinois
Explore the most affordable flight options available from Florida Keys to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 29, 2026.

This CheapOair deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/257:12 am
MIA
-
ORD
Nonstop3h 27m
Spirit Airlines
Thu 2/267:23 pm
ORD
-
MIA
Nonstop3h 16m
Spirit Airlines
Deal found 1/27$72
This Super.com deal was found by Cheapflights users on 1/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/1911:28 am
MIA
-
MDW
Nonstop3h 28m
Frontier
Sun 3/16:15 am
MDW
-
MIA
Nonstop3h 13m
Frontier
Deal found 1/26$72
This Priceline deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/277:00 am
MIA
-
ORD
Nonstop3h 38m
Multiple Airlines
Sun 3/17:23 pm
ORD
-
MIA
Nonstop3h 16m
Multiple Airlines
Deal found 1/28$73
This Trip.com deal was found by Cheapflights users on 1/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2611:28 am
MIA
-
MDW
Nonstop3h 28m
Frontier
Thu 3/56:15 am
MDW
-
MIA
Nonstop3h 13m
Frontier
Deal found 1/26$73
This Spirit deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/193:50 pm
MIA
-
ORD
Nonstop3h 28m
Spirit Airlines
Sun 2/227:23 pm
ORD
-
MIA
Nonstop3h 16m
Spirit Airlines
Deal found 1/27$74
This CheapOair deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2012:40 pm
MIA
-
ORD
Nonstop3h 38m
Multiple Airlines
Sun 2/227:23 pm
ORD
-
MIA
Nonstop3h 16m
Multiple Airlines
Deal found 1/27$78
This Cheapflightsfares deal was found by Cheapflights users on 1/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/147:12 am
MIA
-
ORD
Nonstop3h 27m
Spirit Airlines
Mon 2/169:18 am
ORD
-
MIA
Nonstop3h 18m
Spirit Airlines
Deal found 1/26$81
This Expedia deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/257:12 am
MIA
-
ORD
Nonstop3h 27m
Multiple Airlines
Sat 2/2811:48 am
ORD
-
MIA
Nonstop3h 15m
Multiple Airlines
Deal found 1/28$82
This Flightnetwork deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/247:12 am
MIA
-
ORD
Nonstop3h 27m
Spirit Airlines
Sun 3/17:23 pm
ORD
-
MIA
Nonstop3h 16m
Spirit Airlines
Deal found 1/27$84
This Frontier deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/277:00 am
MIA
-
ORD
Nonstop3h 38m
Frontier
Sat 2/2811:48 am
ORD
-
MIA
Nonstop3h 15m
Frontier
Deal found 1/27$85
This Priceline deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/267:12 am
MIA
-
ORD
Nonstop3h 27m
Multiple Airlines
Sat 2/2811:48 am
ORD
-
MIA
Nonstop3h 15m
Multiple Airlines
Deal found 1/27$86
This Spirit deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/55:54 am
MIA
-
ORD
Nonstop3h 24m
Spirit Airlines
Sun 2/86:57 pm
ORD
-
MIA
Nonstop3h 17m
Spirit Airlines
Deal found 1/27$87

Find flight deals from Florida Keys to Illinois

Keep the following information in mind while searching for Florida Keys to Illinois flight deals. Data was last updated January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$72
(CheapOair)

One-way from

$60
(Trip.com)
Provider with most accurate pricing for Key West-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Key West-Chicago (CHI) flights.
Search Deals
From Florida Keys to Illinois
Search Deals
One-way flight from Florida Keys to Illinois
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Florida Keys to Illinois that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 29, 2026.
Use the filters below to find and compare flights from Florida Keys to Illinois that are best for you.

Fly from

Florida Keys

Fly to

Illinois

Route

Depart

Return

Price

MiamiChicago

MIA - ORD

MIAORD

Miami

Thu 2/26

3:50 pm-6:18 pm

Nonstop3h 28m

Chicago O'Hare Intl

Sun 3/1

7:23 pm-11:39 pm

Nonstop3h 16m

$74

MiamiChicago

MIA - ORD

MIAORD

Miami

Thu 2/19

3:50 pm-6:18 pm

Nonstop3h 28m

Chicago O'Hare Intl

Sat 2/21

8:59 am-8:51 pm

1 stop10h 52m

$95

MiamiChicago

MIA - ORD

MIAORD

Miami

Sat 2/21

9:53 pm-7:54 am

1 stop11h 01m

Chicago O'Hare Intl

Sun 2/22

7:23 pm-11:39 pm

Nonstop3h 16m

$95

MiamiChicago

MIA - ORD

MIAORD

Miami

Fri 2/27

9:53 pm-7:54 am

1 stop11h 01m

Chicago O'Hare Intl

Sun 3/1

7:23 pm-11:39 pm

Nonstop3h 16m

$100

MiamiChicago

MIA - ORD

MIAORD

Miami

Sat 2/14

7:12 am-9:39 am

Nonstop3h 27m

Chicago O'Hare Intl

Sun 2/15

9:18 am-1:36 pm

Nonstop3h 18m

$104

MiamiChicago

MIA - ORD

MIAORD

Miami

Sat 3/14

7:15 am-9:53 am

Nonstop3h 38m

Chicago O'Hare Intl

Wed 3/18

6:01 pm-2:09 am

1 stop7h 08m

$112

MiamiChicago

MIA - ORD

MIAORD

Miami

Sun 2/15

7:12 am-9:39 am

Nonstop3h 27m

Chicago O'Hare Intl

Sun 2/22

8:59 am-8:51 pm

1 stop10h 52m

$123

MiamiChicago

MIA - ORD

MIAORD

Miami

Thu 2/19

9:53 pm-7:54 am

1 stop11h 01m

Chicago O'Hare Intl

Sun 2/22

8:59 am-8:51 pm

1 stop10h 52m

$126

MiamiSt. Louis

MIA - STL

MIASTL

Miami

Wed 4/8

3:12 pm-10:30 am

1 stop20h 18m

Lambert-St Louis

Sun 4/12

11:21 am-10:22 am

1 stop22h 01m

$163

MiamiChicago

MIA - MDW

MIAMDW

Miami

Thu 2/19

5:05 am-11:27 am

1 stop7h 22m

Chicago Midway

Mon 2/23

6:00 am-9:57 pm

2 stops14h 57m

$185

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 60 results
1
2
3
...
6

Best time to book a flight from Florida Keys to Illinois

Have a flexible travel schedule? Discover the best time to fly to Illinois from Florida Keys with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Florida Keys to Illinois

What is the cheapest time of day to fly from EOA to IL?

Find hourly flight availability from Florida Keys to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 29, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Florida Keys to Illinois as you normally would.

Weekly flight availability from Florida Keys to Illinois

Explore weekly flight availability from Florida Keys to Illinois. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated January 29, 2026.

The most flights from zzEOA to USIL are scheduled on a Monday (5 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (3 on average).

Reviews of airlines servicing Illinois

Get insights into the airlines that provide service to Illinois. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Illinois. Reviews last updated January 29, 2026.
Get a feel of what it's like to fly with Southwest, United Airlines, and American Airlines from Florida Keys to Illinois by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,267 reviews

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Southwest
8.0
Very good
4,267 reviews
Southwest
8.0
Very good
4,267 reviews

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
United Airlines
7.4
Good
9,215 reviews
Southwest
8.0
Very good
4,267 reviews

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
American Airlines
7.2
Good
11,205 reviews
Southwest
8.0
Very good
4,267 reviews

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Spirit Airlines
6.3
Okay
8,394 reviews
Southwest
8.0
Very good
4,267 reviews

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Frontier
5.7
Fair
3,056 reviews
Southwest
8.0
Very good
4,267 reviews

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Related info for your journey

Find useful and relevant information for your journey from Florida Keys to Illinois. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Florida Keys to Illinois?

    Airlines like Spirit Airlines, Frontier, and Southwest fly from Florida Keys to Illinois in about 3h 15m. The time it takes to get you to your destination can typically vary by up to 4h 07m. The distance from Florida Keys to Illinois is about 1183 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Florida Keys to Illinois one-way?

    The cheapest airlines for a one-way flight from Florida Keys to Illinois are Spirit Airlines ($43), Frontier ($44), and JetBlue ($71).

  • Can I find deals for flights from Florida Keys to Illinois that include hotel bookings?

    Yes. In addition to deals on Florida Keys to Illinois flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Florida Keys to Illinois?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Florida Keys to Illinois.

  • Can I find deals for business class flights from Florida Keys to Illinois?

    Yes. Cheapflights offers flight deals from Florida Keys to Illinois by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Florida Keys to Illinois

See prices for flight routes from nearby airports that may be better suited for you.
Fort Lauderdale to John F Kennedy Intl flights
Miami to John F Kennedy Intl flights
Fort Lauderdale to Newark flights
Fort Lauderdale to LaGuardia flights
Orlando to John F Kennedy Intl flights
Orlando to Las Vegas flights
Miami to LaGuardia flights
Miami to Newark flights
Fort Lauderdale to Las Vegas flights
Tampa to John F Kennedy Intl flights
Orlando to Los Angeles flights
West Palm Beach to Newark flights
Tampa to LaGuardia flights
Orlando to Newark flights
Orlando to LaGuardia flights
Tampa to Newark flights
Orlando to Denver flights
Miami to Denver flights
West Palm Beach to John F Kennedy Intl flights
Orlando to Seattle flights
Tampa to Seattle flights
Tampa to Las Vegas flights
Miami to Las Vegas flights
Orlando to Dulles Intl flights
Miami to Los Angeles flights
Fort Lauderdale to Atlanta flights
Fort Lauderdale to Denver flights
Miami to Dulles Intl flights
Tampa to Denver flights
West Palm Beach to LaGuardia flights
Tampa to Atlanta flights
Orlando to Dallas/Fort Worth flights
Tampa to Boston flights
Miami to Atlanta flights
Jacksonville to John F Kennedy Intl flights
Tampa to Los Angeles flights
Orlando to Reagan-National flights
Jacksonville to Newark flights
Tampa to Dallas/Fort Worth flights
West Palm Beach to Atlanta flights
Fort Lauderdale to Los Angeles flights
Fort Lauderdale to Dulles Intl flights
Orlando to San Francisco flights
Tampa to Sky Harbor Intl flights
Orlando to Baltimore flights
Orlando to Sky Harbor Intl flights
Miami to Baltimore flights
Orlando to Boston flights
Tampa to Dulles Intl flights
Fort Myers to John F Kennedy Intl flights

Top 2 airlines flying from Florida Keys to Illinois

Discover the top 2 airlines that operate flights from Florida Keys to Illinois. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$249Average$367FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$289Average$427FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.