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O'Hare Intl

$67+ Cheap flights from Florida Keys to O'Hare Intl (ORD)

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 1/11. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — ORD
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
1 adult, Economy
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Cheap flight deals from Florida Keys to O'Hare Intl

Keep the following information in mind while searching for Florida Keys to O'Hare Intl flight deals. Data was last updated November 3, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$98
(Priceline)

One-way from

$67
(Kiwi.com)
Provider with most accurate pricing for Key West-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Key West-Chicago (CHI) flights.
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From Florida Keys to Chicago O'Hare Intl
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One-way flight from Florida Keys to Chicago O'Hare Intl
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Find flight deals from Florida Keys to O'Hare Intl

Cheapest flights from Florida Keys to O'Hare Intl
Explore the most affordable flight options available from Florida Keys to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 3, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/206:21 pmMIA - ORD
1 stop6h 47mMultiple Airlines
Tue 12/211:40 amORD - MIA
Nonstop3h 07mMultiple Airlines
Deal found 11/2$98
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/44:08 pmMIA - ORD
Nonstop3h 28mMultiple Airlines
Thu 12/115:15 amORD - MIA
1 stop11h 40mMultiple Airlines
Deal found 11/1$99
This Spirit deal was found by Cheapflights users on 11/2. 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.
Wed 12/38:10 amMIA - ORD
Nonstop3h 25mSpirit Airlines
Wed 12/33:53 pmORD - MIA
1 stop6h 22mSpirit Airlines
Deal found 11/2$100
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/258:10 amMIA - ORD
Nonstop3h 25mSpirit Airlines
Tue 12/97:41 pmORD - MIA
Nonstop3h 16mSpirit Airlines
Deal found 11/2$101
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/94:08 pmMIA - ORD
Nonstop3h 28mSpirit Airlines
Mon 12/157:41 pmORD - MIA
Nonstop3h 16mSpirit Airlines
Deal found 11/2$102
This Priceline deal was found by Cheapflights users on 11/1. 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 11/208:10 amMIA - ORD
Nonstop3h 25mSpirit Airlines
Fri 11/2811:40 amORD - MIA
Nonstop3h 07mSpirit Airlines
Deal found 11/1$103
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/278:10 amMIA - ORD
Nonstop3h 25mMultiple Airlines
Mon 12/811:01 amORD - MIA
1 stop11h 17mMultiple Airlines
Deal found 11/2$104
This Trip.com deal was found by Cheapflights users on 11/1. 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.
Wed 12/38:10 amMIA - ORD
Nonstop3h 25mMultiple Airlines
Fri 12/124:20 pmORD - MIA
1 stop7h 26mMultiple Airlines
Deal found 11/1$105
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/104:08 pmMIA - ORD
Nonstop3h 28mMultiple Airlines
Sun 12/148:55 amORD - MIA
1 stop8h 00mMultiple Airlines
Deal found 11/2$106
This Cheapflightsfares deal was found by Cheapflights users on 11/2. 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.
Thu 11/208:10 amMIA - ORD
Nonstop3h 25mSpirit Airlines
Sun 11/2311:40 amORD - MIA
Nonstop3h 07mSpirit Airlines
Deal found 11/2$107
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/45:30 amMIA - ORD
1 stop12h 57mMultiple Airlines
Sun 12/77:41 pmORD - MIA
Nonstop3h 16mMultiple Airlines
Deal found 11/2$108
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/95:58 pmMIA - ORD
1 stop21h 33mMultiple Airlines
Tue 12/167:41 pmORD - MIA
Nonstop3h 16mMultiple Airlines
Deal found 11/2$109

Cheapflights Fare Finder

 
Customize your flight search to find flights from Florida Keys to O'Hare Intl 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 November 3, 2025.
Use the filters below to find and compare flights from Florida Keys to Chicago O'Hare Intl Airport that are best for you.

Fly from

Florida Keys

Fly to

O'Hare Intl

Route

Depart

Return

Price

Key WestChicago

EYW - ORD

EYWORD

Key West

Fri 12/5

8:55 am-1:16 pm

1 stop29h 21m

Chicago O'Hare Intl

Tue 12/9

7:10 am-3:41 pm

2 stops31h 31m

$202

MiamiChicago

MIA - ORD

MIAORD

Miami

Sat 12/6

8:10 am-1:50 pm

1 stop6h 40m

Chicago O'Hare Intl

Sun 12/7

9:52 am-5:25 pm

1 stop6h 33m

$217

MiamiChicago

MIA - ORD

MIAORD

Miami

Sat 12/6

6:00 am-10:22 am

1 stop5h 22m

Chicago O'Hare Intl

Wed 1/14

11:05 am-5:48 pm

1 stop5h 43m

$217

Key WestChicago

EYW - ORD

EYWORD

Key West

Fri 12/5

2:47 pm-11:32 pm

1 stop9h 45m

Chicago O'Hare Intl

Tue 12/9

11:05 am-3:24 pm

Nonstop3h 19m

$259

Key WestChicago

EYW - ORD

EYWORD

Key West

Mon 11/24

6:18 pm-12:02 am

1 stop6h 44m

Chicago O'Hare Intl

Sat 11/29

11:15 am-5:23 pm

1 stop5h 08m

$269

Key WestChicago

EYW - ORD

EYWORD

Key West

Mon 11/24

6:18 pm-12:02 am

1 stop6h 44m

Chicago O'Hare Intl

Sun 11/30

6:45 am-2:03 pm

1 stop6h 18m

$269

Key WestChicago

EYW - ORD

EYWORD

Key West

Sun 11/16

10:59 am-5:15 pm

2 stops31h 16m

Chicago O'Hare Intl

Sun 11/23

7:09 pm-8:15 am

1 stop12h 06m

$272

MiamiChicago

MIA - ORD

MIAORD

Miami

Wed 11/19

7:00 am-9:29 am

Nonstop3h 29m

Chicago O'Hare Intl

Thu 11/27

10:35 am-2:51 pm

Nonstop3h 16m

$287

MiamiChicago

MIA - ORD

MIAORD

Miami

Wed 12/24

10:32 am-4:21 pm

1 stop6h 49m

Chicago O'Hare Intl

Sun 12/28

5:29 pm-12:48 am

1 stop6h 19m

$295

MiamiChicago

MIA - ORD

MIAORD

Miami

Wed 12/24

12:45 pm-7:38 pm

1 stop7h 53m

Chicago O'Hare Intl

Mon 12/29

1:35 pm-11:06 pm

1 stop8h 31m

$295

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/31

Showing 1-10 of 40 results
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Best time to book a flight from Florida Keys to O'Hare Intl

Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl 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 Chicago O'Hare Intl Airport

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

Find hourly flight availability from Florida Keys to O'Hare Intl. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 3, 2025.

It’s typically best to fly out from Florida Keys to Chicago O'Hare Intl Airport at noon. Doing so could potentially save you 34% on the flight price compared to flying in the evening, which is usually more expensive.

Weekly flight availability from Florida Keys to Chicago O'Hare Intl Airport

Explore weekly flight availability from Florida Keys to O'Hare Intl. 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 November 3, 2025.

The most flights from zzEOA to ORD are scheduled on a Monday (4 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (2 on average).

Reviews of airlines servicing O'Hare Intl

Get insights into the airlines that provide service to O'Hare Intl. 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 O'Hare Intl. Reviews last updated November 3, 2025.
Read through reviews of airlines operating flights from Florida Keys to Chicago O'Hare Intl Airport, such as United Airlines, American Airlines, and Spirit Airlines. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,997 reviews

Entertainment

7.1

Food

6.6

Boarding

7.7

Comfort

7.3

Overall

7.4

Crew

8.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
8,997 reviews
United Airlines
7.4
Good
8,997 reviews

Entertainment

7.1

Food

6.6

Boarding

7.7

Comfort

7.3

Overall

7.4

Crew

8.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
American Airlines
7.2
Good
11,036 reviews
United Airlines
7.4
Good
8,997 reviews

Entertainment

7.1

Food

6.6

Boarding

7.7

Comfort

7.3

Overall

7.4

Crew

8.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
Spirit Airlines
6.3
Okay
8,114 reviews
United Airlines
7.4
Good
8,997 reviews

Entertainment

7.1

Food

6.6

Boarding

7.7

Comfort

7.3

Overall

7.4

Crew

8.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
Frontier
5.8
Fair
3,117 reviews
United Airlines
7.4
Good
8,997 reviews

Entertainment

7.1

Food

6.6

Boarding

7.7

Comfort

7.3

Overall

7.4

Crew

8.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

Related info for your journey

Find useful and relevant information for your journey from Florida Keys to O'Hare Intl. 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 Chicago O'Hare Intl Airport?

    A quick flight from Florida Keys to Chicago O'Hare Intl Airport can take about 3h 29m. Delta provides one of the quickest options available for as low as $297. The distance from Florida Keys to Chicago O'Hare Intl Airport is about 1198 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Florida Keys to Chicago O'Hare Intl Airport one-way?

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $72. Spirit Airlines flights start at $75 while deals on United Airlines start at $79 one-way.

  • What are the most reliable airlines from Florida Keys to Chicago O'Hare Intl Airport?

    Before booking your flight to Chicago O'Hare Intl Airport from Florida Keys, check out the most reliable airlines to get you to your destination on time: United Airlines (83%), Air New Zealand (83%), Republic Airways( 83%).

  • What are the cheapest flights from Florida Keys to Chicago O'Hare Intl Airport?

    Looking at all options, your cheapest flight can be booked for $201. While the most popular route (Miami - Chicago O'Hare Intl) can be booked for $74 on average, our data indicates $588 when flying from Florida Keys to Chicago O'Hare Intl Airport.

  • Can I find deals for flights from Florida Keys to O'Hare Intl that include hotel bookings?

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

  • How can I find direct flights from Florida Keys to O'Hare Intl?

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

  • Can I find deals for business class flights from Florida Keys to O'Hare Intl?

    Yes. Cheapflights offers flight deals from Florida Keys to O'Hare Intl 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

Traveling to a place near Chicago O'Hare Intl Airport?

Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locations
Schaumburg
Rosemont
Skokie
Des Plaines
Gurnee
Hoffman Estates
Beloit
Elgin
Oak Brook
Elk Grove Village
Naperville
Racine
Downers Grove
Rockford
Orland Park
Merrillville
Bridgeview
Warrenville
Waukegan
Aurora

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Alternative routes for Florida Keys to O'Hare Intl

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Florida Keys to O'Hare Intl

Discover the top 2 airlines that operate flights from Florida Keys to O'Hare Intl. 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 November 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$224Average$499FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$289Average$398FlexibilityNo cancel feeOn-time71%

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