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Cheap flights from Florida Keys to Chicago from $62

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Florida Keys to Chicago departing on 5/2. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Florida Keys to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Spirit Airlines Logo
9:30 pm - 11:56 pm
MIA
-
ORD
3h 26mnonstop
Spirit Airlines Logo
9:20 am - 1:28 pm
ORD
-
MIA
3h 08mnonstop
$88Spirit Airlines
Fri, May 8 - Mon, May 11
Multiple Airlines Logo
6:30 am - 5:11 pm
MIA
-
ORD
11h 41m
1 stop
Multiple Airlines Logo
3:52 pm - 8:11 pm
ORD
-
MIA
3h 19mnonstop
$89Multiple Airlines
Tue, Apr 28 - Sun, May 3
Spirit Airlines Logo
10:41 am - 1:05 pm
MIA
-
ORD
3h 24mnonstop
Spirit Airlines Logo
9:20 am - 1:28 pm
ORD
-
MIA
3h 08mnonstop
$90Spirit Airlines
Fri, May 1 - Mon, May 4
Spirit Airlines Logo
10:41 am - 1:05 pm
MIA
-
ORD
3h 24mnonstop
Spirit Airlines Logo
7:50 am - 11:58 am
ORD
-
MIA
3h 08mnonstop
$91Spirit Airlines
Fri, Apr 24 - Mon, Apr 27
Multiple Airlines Logo
6:30 am - 5:11 pm
MIA
-
ORD
11h 41m
1 stop
Multiple Airlines Logo
3:52 pm - 8:11 pm
ORD
-
MIA
3h 19mnonstop
$92Multiple Airlines
Fri, May 1 - Sun, May 3
Frontier Logo
5:05 am - 11:32 am
MIA
-
ORD
7h 27m
1 stop
Frontier Logo
3:52 pm - 8:11 pm
ORD
-
MIA
3h 19mnonstop
$97Frontier
Thu, Apr 30 - Sat, May 2
Frontier Logo
2:13 pm - 4:50 pm
MIA
-
ORD
3h 37mnonstop
Frontier Logo
8:39 am - 10:27 am
ORD
-
MIA
24h 48m
1 stop
$98Frontier
Thu, May 7 - Thu, May 14
American Airlines Logo
1:08 pm - 3:55 pm
EYW
-
ORD
3h 47mnonstop
American Airlines Logo
1:50 pm - 6:16 pm
ORD
-
EYW
3h 26mnonstop
$369American Airlines
Wed, Apr 22 - Sun, Apr 26
American Airlines Logo
11:56 am - 4:21 pm
EYW
-
ORD
5h 25m
1 stop
American Airlines Logo
1:50 pm - 6:16 pm
ORD
-
EYW
3h 26mnonstop
$379American Airlines
Wed, Apr 22 - Sun, Apr 26
United Airlines Logo
6:22 pm - 11:43 pm
EYW
-
ORD
6h 21m
1 stop
United Airlines Logo
7:00 am - 5:39 pm
ORD
-
EYW
9h 39m
1 stop
$389United Airlines
Sat, Apr 25 - Wed, Apr 29

Frontier flights from Florida Keys to Chicago O'Hare Intl Airport

Our best Frontier deals on Florida Keys to Chicago O'Hare Intl Airport flight tickets
Frontier
Apr 16
MIA9:21 pmMiami
3h 38m
ORD11:59 pmChicago O'Hare Intl
Apr 19
ORD3:52 pmChicago O'Hare Intl
3h 19m
MIA8:11 pmMiami
$88
Frontier
Apr 20
MIA10:17 pmMiami
3h 38m
ORD12:55 amChicago O'Hare Intl
May 3
ORD3:52 pmChicago O'Hare Intl
3h 19m
MIA8:11 pmMiami
$97
Frontier
May 7
MIA5:05 amMiami
10h 34m
1 stop
ORD2:39 pmChicago O'Hare Intl
May 10
ORD5:49 pmChicago O'Hare Intl
3h 18m
MIA10:07 pmMiami
$107

Spirit Airlines flights from Florida Keys to Chicago O'Hare Intl Airport

Our best Spirit Airlines deals on Florida Keys to Chicago O'Hare Intl Airport flight tickets
Spirit Airlines
May 1
MIA10:41 amMiami
3h 24m
ORD1:05 pmChicago O'Hare Intl
May 4
ORD9:20 amChicago O'Hare Intl
3h 08m
MIA1:28 pmMiami
$90
Spirit Airlines
Apr 24
MIA10:41 amMiami
3h 24m
ORD1:05 pmChicago O'Hare Intl
Apr 27
ORD7:50 amChicago O'Hare Intl
3h 08m
MIA11:58 amMiami
$91
Spirit Airlines
Apr 24
MIA10:41 amMiami
3h 24m
ORD1:05 pmChicago O'Hare Intl
Apr 27
ORD7:50 amChicago O'Hare Intl
3h 08m
MIA11:58 amMiami
$95

momondo Fare Finder

 
Customize your flight search to find flights from Florida Keys to Chicago O'Hare Intl Airport 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, momondo users made 832,500 searches. Data last updated April 12, 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

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MiamiChicago

MIA - ORD

MIAORD

Miami

Fri 5/8

9:30 pm-11:56 pm

Nonstop3h 26m

Chicago O'Hare Intl

Mon 5/11

9:20 am-1:28 pm

Nonstop3h 08m

$88

MiamiChicago

MIA - ORD

MIAORD

Miami

Tue 4/28

6:30 am-5:11 pm

1 stop11h 41m

Chicago O'Hare Intl

Sun 5/3

3:52 pm-8:11 pm

Nonstop3h 19m

$89
Quickest round-trip

MiamiChicago

MIA - ORD

MIAORD

Miami

Fri 5/1

10:41 am-1:05 pm

Nonstop3h 24m

Chicago O'Hare Intl

Mon 5/4

9:20 am-1:28 pm

Nonstop3h 08m

$90

MiamiChicago

MIA - ORD

MIAORD

Miami

Fri 4/24

10:41 am-1:05 pm

Nonstop3h 24m

Chicago O'Hare Intl

Mon 4/27

7:50 am-11:58 am

Nonstop3h 08m

$91

MiamiChicago

MIA - ORD

MIAORD

Miami

Fri 5/1

6:30 am-5:11 pm

1 stop11h 41m

Chicago O'Hare Intl

Sun 5/3

3:52 pm-8:11 pm

Nonstop3h 19m

$92

MiamiChicago

MIA - ORD

MIAORD

Miami

Thu 4/30

5:05 am-11:32 am

1 stop7h 27m

Chicago O'Hare Intl

Sat 5/2

3:52 pm-8:11 pm

Nonstop3h 19m

$97

MiamiChicago

MIA - ORD

MIAORD

Miami

Thu 5/7

2:13 pm-4:50 pm

Nonstop3h 37m

Chicago O'Hare Intl

Thu 5/14

8:39 am-10:27 am

1 stop24h 48m

$98

Key WestChicago

EYW - ORD

EYWORD

Key West

Wed 4/22

1:08 pm-3:55 pm

Nonstop3h 47m

Chicago O'Hare Intl

Sun 4/26

1:50 pm-6:16 pm

Nonstop3h 26m

$369

Key WestChicago

EYW - ORD

EYWORD

Key West

Wed 4/22

11:56 am-4:21 pm

1 stop5h 25m

Chicago O'Hare Intl

Sun 4/26

1:50 pm-6:16 pm

Nonstop3h 26m

$379

Key WestChicago

EYW - ORD

EYWORD

Key West

Sat 4/25

6:22 pm-11:43 pm

1 stop6h 21m

Chicago O'Hare Intl

Wed 4/29

7:00 am-5:39 pm

1 stop9h 39m

$389

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Florida Keys to Chicago O'Hare Intl Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago O'Hare Intl Airport?

The month of October is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Florida Keys averaging around $178.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Friday when prices can be found for as low as $297. This is often the case because there is less demand to fly during this day of the week. On the other hand, Monday is the most expensive day to depart from Florida Keys because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $533.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from Florida Keys in the evening is the least expensive time of day to depart. momondo users have found prices as low as $335 when looking at flights departing in the evening. Try not to purchase tickets in the afternoon because they tend to be around $390. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Florida Keys to Chicago O'Hare Intl flight route?

Fly from Key West to Chicago O'Hare Intl for the best Florida Keys - Chicago O'Hare Intl flight prices

How far in advance should I book a flight to Chicago O'Hare Intl Airport?

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Florida Keys when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $240 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from Florida Keys for as low as $165 on momondo.

What cabin class options are available on Florida Keys to Chicago O'Hare Intl flights?

There are 4 cabin classes available to choose from on Florida Keys to Chicago O'Hare Intl flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Florida Keys to Chicago O'Hare Intl Airport flights?

No. A direct flight is the cheapest option for a flight between Florida Keys to Chicago O'Hare Intl Airport.

Cheap Florida Keys to Chicago O'Hare Intl Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Florida Keys to Chicago O'Hare Intl Airport

Fastest flight time

3h 10m

Direct flights

Every day
The fastest flight from Florida Keys to Chicago O'Hare Intl Airport takes 3h 10m
Direct flights go from Florida Keys to Chicago O'Hare Intl Airport every day.
Search flight deals

Frequently asked questions about flying from Florida Keys to Chicago O'Hare Intl Airport

  • When did momondo last update prices for flights from Florida Keys to Chicago O'Hare Intl Airport?

    Prices for flights from Florida Keys to Chicago O'Hare Intl Airport were last updated today.

  • How many operators does momondo search for flights from Florida Keys to Chicago O'Hare Intl Airport?

  • How old do you have to be to fly from Florida Keys to Chicago O'Hare Intl Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Florida Keys to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The travel and health documents you'll need for your trip to Chicago O'Hare Intl Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago O'Hare Intl Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Florida Keys to Chicago O'Hare Intl Airport?

Best airlines flying from Florida Keys to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Florida Keys to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $249Free CancellationRating
7.4
9,574 reviews
Search United Airlines flights
American AirlinesPriceFrom $344Free CancellationRating
7.1
11,570 reviews
Search American Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
Schaumburg
South Haven
Rockford
Merrillville
Gurnee
Rosemont
Naperville
New Buffalo
Orland Park
Oak Brook
Kenosha
Joliet
Aurora
Janesville
Racine
Hammond
Elgin
Tinley Park
Evanston

Why use momondo?

Why should I use momondo to find a flight deal from Florida Keys to Chicago?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Florida Keys to Chicago for you.

Can I find flights from Florida Keys to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from Florida Keys with this policy.

How can momondo help me find flights from Florida Keys to Chicago?

momondo provides multiple filters to help you find the best flight to Chicago from Florida Keys. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Florida Keys to Chicago right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Chicago from Florida Keys. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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