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Cheap flights from Florida Keys to Chicago from $63

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 9/17. 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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Cheap round-trip flights

Spirit Airlines Logo
7:00 am - 9:18 amMIA-ORD
3h 18mnonstop
Spirit Airlines Logo
10:27 am - 2:39 pmORD-MIA
3h 12mnonstop
$108Spirit Airlines
Find Deal
lun., sep. 22 - vie., sep. 26
Spirit Airlines Logo
7:00 am - 9:22 amMIA-ORD
3h 22mnonstop
Spirit Airlines Logo
10:27 am - 2:29 pmORD-MIA
3h 02mnonstop
$109Spirit Airlines
Find Deal
jue., oct. 23 - vie., oct. 24
Logo
7:00 am - 9:18 amMIA-ORD
3h 18mnonstop
Logo
9:35 am - 6:28 pmORD-MIA
7h 53m1 stop
$111
Find Deal
jue., oct. 2 - vie., oct. 3
Logo
6:00 am - 8:18 amMIA-ORD
3h 18mnonstop
Logo
11:50 am - 12:54 amORD-MIA
12h 04m1 stop
$113
Find Deal
sáb., nov. 1 - jue., nov. 6
Frontier Logo
6:00 am - 1:12 pmMIA-ORD
8h 12m1 stop
Frontier Logo
7:40 am - 12:42 amORD-MIA
16h 02m1 stop
$141Frontier
Find Deal
jue., sep. 18 - dom., sep. 21
Frontier Logo
4:01 pm - 11:20 pmMIA-ORD
8h 19m1 stop
Frontier Logo
7:40 am - 12:42 amORD-MIA
16h 02m1 stop
$142Frontier
Find Deal
vie., sep. 19 - lun., sep. 22
United Airlines Logo
6:45 am - 9:14 amMIA-ORD
3h 29mnonstop
United Airlines Logo
7:35 am - 11:49 amORD-MIA
3h 14mnonstop
$157United Airlines
Find Deal
sáb., nov. 15 - lun., nov. 17
United Airlines Logo
4:05 pm - 6:30 pmEYW-ORD
3h 25mnonstop
United Airlines Logo
10:55 am - 3:06 pmORD-EYW
3h 11mnonstop
$417United Airlines
Find Deal
vie., feb. 27 - mar., mar. 3
American Airlines Logo
11:25 am - 7:05 pmEYW-ORD
8h 40m2 stops
American Airlines Logo
6:09 am - 1:29 pmORD-EYW
6h 20m1 stop
$419American Airlines
Find Deal
mié., sep. 17 - dom., sep. 21
American Airlines Logo
1:17 pm - 3:57 pmEYW-ORD
3h 40mnonstop
American Airlines Logo
12:02 pm - 4:25 pmORD-EYW
3h 23mnonstop
$461American Airlines
Find Deal
lun., nov. 24 - sáb., nov. 29

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
Sep 22
MIA7:00 amMiami
3h 18m
ORD9:18 amChicago O'Hare Intl
Sep 26
ORD10:27 amChicago O'Hare Intl
3h 12m
MIA2:39 pmMiami
$108
Find similar
Spirit Airlines
Oct 23
MIA7:00 amMiami
3h 22m
ORD9:22 amChicago O'Hare Intl
Oct 24
ORD10:27 amChicago O'Hare Intl
3h 02m
MIA2:29 pmMiami
$109
Find similar
Spirit Airlines
Sep 26
MIA7:00 amMiami
3h 18m
ORD9:18 amChicago O'Hare Intl
Oct 7
ORD10:27 amChicago O'Hare Intl
3h 02m
MIA2:29 pmMiami
$112
Find similar

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

Our best Delta deals on Florida Keys to Chicago O'Hare Intl Airport flight tickets
Delta
Sep 24
EYW11:50 amKey West
8h 10m
1 stop
ORD7:00 pmChicago O'Hare Intl
Sep 29
ORD11:20 amChicago O'Hare Intl
4h 55m
1 stop
EYW5:15 pmKey West
$269
Find similar
Delta
Feb 27
EYW6:00 pmKey West
6h 54m
1 stop
ORD11:54 pmChicago O'Hare Intl
Mar 3
ORD5:50 amChicago O'Hare Intl
6h 22m
1 stop
EYW1:12 pmKey West
$289
Find similar
Delta
Sep 19
EYW6:10 pmKey West
6h 44m
1 stop
ORD11:54 pmChicago O'Hare Intl
Sep 23
ORD7:20 amChicago O'Hare Intl
4h 42m
1 stop
EYW1:02 pmKey West
$309
Find similar

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 septiembre 4, 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

Fly to

Route

Depart

Return

Price

MiamiChicago

MIA - ORD

MIAORD

Miami

lun. 9/22

7:00 am-9:18 am

Nonstop3h 18m

Chicago O'Hare Intl

vie. 9/26

10:27 am-2:39 pm

Nonstop3h 12m

$108

MiamiChicago

MIA - ORD

MIAORD

Miami

jue. 10/23

7:00 am-9:22 am

Nonstop3h 22m

Chicago O'Hare Intl

vie. 10/24

10:27 am-2:29 pm

Nonstop3h 02m

$109

MiamiChicago

MIA - ORD

MIAORD

Miami

jue. 10/2

7:00 am-9:18 am

Nonstop3h 18m

Chicago O'Hare Intl

vie. 10/3

9:35 am-6:28 pm

1 stop7h 53m

$111

MiamiChicago

MIA - ORD

MIAORD

Miami

sáb. 11/1

6:00 am-8:18 am

Nonstop3h 18m

Chicago O'Hare Intl

jue. 11/6

11:50 am-12:54 am

1 stop12h 04m

$113

MiamiChicago

MIA - ORD

MIAORD

Miami

jue. 9/18

6:00 am-1:12 pm

1 stop8h 12m

Chicago O'Hare Intl

dom. 9/21

7:40 am-12:42 am

1 stop16h 02m

$141

MiamiChicago

MIA - ORD

MIAORD

Miami

vie. 9/19

4:01 pm-11:20 pm

1 stop8h 19m

Chicago O'Hare Intl

lun. 9/22

7:40 am-12:42 am

1 stop16h 02m

$142

MiamiChicago

MIA - ORD

MIAORD

Miami

sáb. 11/15

6:45 am-9:14 am

Nonstop3h 29m

Chicago O'Hare Intl

lun. 11/17

7:35 am-11:49 am

Nonstop3h 14m

$157

Key WestChicago

EYW - ORD

EYWORD

Key West

vie. 2/27

4:05 pm-6:30 pm

Nonstop3h 25m

Chicago O'Hare Intl

mar. 3/3

10:55 am-3:06 pm

Nonstop3h 11m

$417

Key WestChicago

EYW - ORD

EYWORD

Key West

mié. 9/17

11:25 am-7:05 pm

2 stops8h 40m

Chicago O'Hare Intl

dom. 9/21

6:09 am-1:29 pm

1 stop6h 20m

$419

Key WestChicago

EYW - ORD

EYWORD

Key West

lun. 11/24

1:17 pm-3:57 pm

Nonstop3h 40m

Chicago O'Hare Intl

sáb. 11/29

12:02 pm-4:25 pm

Nonstop3h 23m

$461

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 February is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Florida Keys averaging around $218.

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 $305. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday 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 $482.

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 $287 when looking at flights departing in the evening. Try not to purchase tickets in the afternoon because they tend to be around $393. 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 $250 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 $202 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 15m

Direct flights

Every day
The fastest flight from Florida Keys to Chicago O'Hare Intl Airport takes 3h 15m
Direct flights go from Florida Keys to Chicago O'Hare Intl Airport every day.
Search flight deals

  • 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 $224Free CancellationRating
7.4
8,937 reviews
Search United Airlines flights
American AirlinesPriceFrom $259Free CancellationRating
7.2
10,000 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
South Haven
Rockford
Schaumburg
Merrillville
Gurnee
Naperville
Rosemont
Kenosha
New Buffalo
Joliet
Oak Brook
Racine
Hammond
Orland Park
Tinley Park
Elgin
Aurora
Janesville
Benton Harbor

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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