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O'Hare Intl

$50+ 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 3/9. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — ORD
Mar 23 — Mar 301
Mon 3/23
Mon 3/30
1 adult, Economy
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Cheap 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 February 21, 2026.

This Cheapflightsfares deal was found by Cheapflights users on 2/17. 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 2/218:00 am
MIA
-
ORD
Nonstop3h 38m
Frontier
Mon 2/2311:33 am
ORD
-
MIA
Nonstop3h 15m
Frontier
Deal found 2/17$73
This Expedia deal was found by Cheapflights users on 2/17. 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 3/117:12 am
MIA
-
ORD
Nonstop3h 27m
Spirit Airlines
Tue 3/1710:55 am
ORD
-
MIA
Nonstop3h 05m
Spirit Airlines
Deal found 2/17$75
This Cheapflightsfares deal was found by Cheapflights users on 2/20. 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 4/169:21 pm
MIA
-
ORD
Nonstop3h 38m
Frontier
Sun 4/193:52 pm
ORD
-
MIA
Nonstop3h 19m
Frontier
Deal found 2/20$76
This Kiwi.com deal was found by Cheapflights users on 2/17. 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 4/97:20 am
MIA
-
ORD
Nonstop3h 30m
Multiple Airlines
Mon 4/1311:59 am
ORD
-
MIA
Nonstop3h 19m
Multiple Airlines
Deal found 2/17$77
This Frontier deal was found by Cheapflights users on 2/17. 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.
Thu 4/239:21 pm
MIA
-
ORD
Nonstop3h 38m
Frontier
Sun 5/33:52 pm
ORD
-
MIA
Nonstop3h 19m
Frontier
Deal found 2/17$78
This Kiwi.com deal was found by Cheapflights users on 2/20. 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.
Sat 3/147:15 am
MIA
-
ORD
Nonstop3h 38m
Frontier
Mon 3/169:50 am
ORD
-
MIA
Nonstop3h 15m
Frontier
Deal found 2/20$79
This CheapOair deal was found by Cheapflights users on 2/20. 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.
Sat 3/146:00 am
MIA
-
ORD
Nonstop3h 25m
Spirit Airlines
Mon 3/234:51 pm
ORD
-
MIA
Nonstop3h 06m
Spirit Airlines
Deal found 2/20$80
This Booking.com deal was found by Cheapflights users on 2/21. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/146:00 am
MIA
-
ORD
Nonstop3h 25m
Multiple Airlines
Mon 3/169:50 am
ORD
-
MIA
Nonstop3h 15m
Multiple Airlines
Deal found 2/21$81
This Frontier deal was found by Cheapflights users on 2/18. 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.
Thu 4/239:21 pm
MIA
-
ORD
Nonstop3h 38m
Frontier
Sat 5/23:52 pm
ORD
-
MIA
Nonstop3h 19m
Frontier
Deal found 2/18$83
This Frontier deal was found by Cheapflights users on 2/20. 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.
Mon 4/2010:17 pm
MIA
-
ORD
Nonstop3h 38m
Frontier
Sun 5/33:52 pm
ORD
-
MIA
Nonstop3h 19m
Frontier
Deal found 2/20$84
This CheapOair deal was found by Cheapflights users on 2/20. 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 3/136:00 am
MIA
-
ORD
Nonstop3h 25m
Multiple Airlines
Mon 3/169:50 am
ORD
-
MIA
Nonstop3h 15m
Multiple Airlines
Deal found 2/20$85
This Delta deal was found by Cheapflights users on 2/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/306:23 pm
EYW
-
ORD
1 stop6h 36m
Delta
Mon 5/45:15 am
ORD
-
EYW
1 stop4h 31m
Delta
Deal found 2/17$187

Find 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 February 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$75
(Expedia)

One-way from

$50
(CheapOair)
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 Chicago O'Hare Intl
Search Deals
One-way flight from Florida Keys to Chicago O'Hare Intl
Search Deals

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 February 21, 2026.
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

MiamiChicago

MIA - ORD

MIAORD

Miami

Thu 3/5

7:12 am-9:39 am

Nonstop3h 27m

Chicago O'Hare Intl

Sun 3/8

7:23 pm-11:39 pm

Nonstop3h 16m

$87

MiamiChicago

MIA - ORD

MIAORD

Miami

Wed 3/4

9:53 pm-7:54 am

1 stop11h 01m

Chicago O'Hare Intl

Sun 3/8

9:18 am-1:36 pm

Nonstop3h 18m

$158

MiamiChicago

MIA - ORD

MIAORD

Miami

Fri 3/13

6:00 am-8:25 am

Nonstop3h 25m

Chicago O'Hare Intl

Sun 3/15

10:55 am-3:00 pm

Nonstop3h 05m

$165

MiamiChicago

MIA - ORD

MIAORD

Miami

Thu 3/19

6:00 am-8:25 am

Nonstop3h 25m

Chicago O'Hare Intl

Sun 3/22

4:51 pm-8:57 pm

Nonstop3h 06m

$190

MiamiChicago

MIA - ORD

MIAORD

Miami

Tue 8/4

8:35 pm-9:09 am

1 stop13h 34m

Chicago O'Hare Intl

Tue 8/11

7:34 am-8:51 pm

1 stop12h 17m

$216

MiamiChicago

MIA - ORD

MIAORD

Miami

Wed 4/22

12:13 pm-4:18 pm

1 stop5h 05m

Chicago O'Hare Intl

Tue 4/28

9:50 am-3:35 pm

1 stop4h 45m

$217

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 3/12

12:25 pm-5:15 pm

1 stop5h 50m

Chicago O'Hare Intl

Mon 3/16

5:05 am-1:37 pm

1 stop7h 32m

$223

MiamiChicago

MIA - ORD

MIAORD

Miami

Sat 3/28

6:00 am-10:06 am

1 stop5h 06m

Chicago O'Hare Intl

Wed 4/1

5:59 pm-12:52 am

1 stop5h 53m

$237

MiamiChicago

MIA - ORD

MIAORD

Miami

Tue 4/21

9:15 am-4:04 pm

1 stop7h 49m

Chicago O'Hare Intl

Wed 4/22

6:25 pm-10:45 pm

Nonstop3h 20m

$243

MiamiChicago

MIA - ORD

MIAORD

Miami

Wed 5/13

6:15 am-12:37 pm

1 stop7h 22m

Chicago O'Hare Intl

Wed 5/13

6:13 pm-10:33 pm

Nonstop3h 20m

$243

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/17

Showing 1-10 of 35 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 February 21, 2026.

When flying from Florida Keys to Chicago O'Hare Intl Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 February 21, 2026.

The most flights from zzEOA to ORD are scheduled on a Monday (7 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (3 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 February 21, 2026.
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
9,335 reviews

Entertainment

7.1

Boarding

7.7

Comfort

7.3

Crew

8.1

Food

6.6

Overall

7.4

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
9,335 reviews
United Airlines
7.4
Good
9,335 reviews

Entertainment

7.1

Boarding

7.7

Comfort

7.3

Crew

8.1

Food

6.6

Overall

7.4

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
11,335 reviews
United Airlines
7.4
Good
9,335 reviews

Entertainment

7.1

Boarding

7.7

Comfort

7.3

Crew

8.1

Food

6.6

Overall

7.4

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
8,482 reviews
United Airlines
7.4
Good
9,335 reviews

Entertainment

7.1

Boarding

7.7

Comfort

7.3

Crew

8.1

Food

6.6

Overall

7.4

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
5.7
Fair
3,046 reviews
United Airlines
7.4
Good
9,335 reviews

Entertainment

7.1

Boarding

7.7

Comfort

7.3

Crew

8.1

Food

6.6

Overall

7.4

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 27m. Spirit Airlines provides one of the quickest options available for as low as $87. 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 Spirit Airlines, which is currently one of the cheapest options available, starting at $42. Frontier flights start at $52 while deals on JetBlue start at $71 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: Republic Airways (98%), United Airlines (82%), Air New Zealand( 73%).

  • 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 $248. While the most popular route (Miami - Chicago O'Hare Intl) can be booked for $68 on average, our data indicates $498 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
Gurnee
Naperville
Hoffman Estates
Beloit
Delavan
Oak Brook
Des Plaines
Elgin
Downers Grove
Elk Grove Village
Skokie
Libertyville
Oakbrook Terrace
Lake Geneva
Waukegan
Bridgeview
Kenosha
Warrenville

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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 February 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$249Average$315FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$309Average$457FlexibilityNo cancel feeOn-time71%

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