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Cheap flights from Florida Keys to Chicago from $67

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 10/29. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
Spirit Airlines Logo
8:10 am - 10:35 amMIA-ORD
3h 25mnonstop
Spirit Airlines Logo
7:41 pm - 11:57 pmORD-MIA
3h 16mnonstop
$96Spirit Airlines
Find Deal
Tue, Nov 25 - Sun, Dec 7
Spirit Airlines Logo
4:08 pm - 6:36 pmMIA-ORD
3h 28mnonstop
Spirit Airlines Logo
7:41 pm - 11:57 pmORD-MIA
3h 16mnonstop
$97Spirit Airlines
Find Deal
Thu, Dec 4 - Thu, Dec 11
Multiple Airlines Logo
7:09 pm - 12:01 amMIA-ORD
5h 52m1 stop
Multiple Airlines Logo
1:35 pm - 5:50 pmORD-MIA
3h 15mnonstop
$112Multiple Airlines
Find Deal
Fri, Jan 9 - Wed, Jan 14
Multiple Airlines Logo
10:15 pm - 10:30 amMIA-ORD
13h 15m1 stop
Multiple Airlines Logo
12:17 pm - 4:22 pmORD-MIA
3h 05mnonstop
$113Multiple Airlines
Find Deal
Fri, Nov 7 - Mon, Nov 10
Frontier Logo
9:03 pm - 2:57 pmMIA-ORD
18h 54m1 stop
Frontier Logo
6:00 am - 5:14 pmORD-MIA
10h 14m1 stop
$129Frontier
Find Deal
Thu, Dec 4 - Sun, Dec 7
Frontier Logo
5:30 am - 10:24 pmMIA-ORD
17h 54m1 stop
Frontier Logo
6:40 am - 8:51 pmORD-MIA
13h 11m1 stop
$130Frontier
Find Deal
Sat, Dec 6 - Wed, Jan 14
United Airlines Logo
3:56 pm - 6:35 pmEYW-ORD
3h 39mnonstop
United Airlines Logo
9:15 am - 5:54 pmORD-EYW
7h 39m1 stop
$295United Airlines
Find Deal
Thu, Feb 26 - Mon, Mar 2
United Airlines Logo
3:56 pm - 6:35 pmEYW-ORD
3h 39mnonstop
United Airlines Logo
10:44 am - 3:00 pmORD-EYW
3h 16mnonstop
$349United Airlines
Find Deal
Thu, Feb 26 - Mon, Mar 2
American Airlines Logo
2:11 pm - 4:51 pmEYW-ORD
3h 40mnonstop
American Airlines Logo
5:00 am - 1:27 pmORD-EYW
7h 27m1 stop
$361American Airlines
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Tue, Nov 4 - Sat, Nov 8
American Airlines Logo
4:00 pm - 6:36 pmEYW-ORD
3h 36mnonstop
American Airlines Logo
8:00 am - 12:22 pmORD-EYW
3h 22mnonstop
$385American Airlines
Find Deal
Thu, Feb 26 - Mon, Mar 2

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
Nov 25
MIA8:10 amMiami
3h 25m
ORD10:35 amChicago O'Hare Intl
Dec 7
ORD7:41 pmChicago O'Hare Intl
3h 16m
MIA11:57 pmMiami
$96
Find similar
Spirit Airlines
Dec 4
MIA4:08 pmMiami
3h 28m
ORD6:36 pmChicago O'Hare Intl
Dec 11
ORD7:41 pmChicago O'Hare Intl
3h 16m
MIA11:57 pmMiami
$97
Find similar
Spirit Airlines
Dec 5
MIA4:08 pmMiami
3h 28m
ORD6:36 pmChicago O'Hare Intl
Dec 12
ORD7:41 pmChicago O'Hare Intl
3h 16m
MIA11:57 pmMiami
$98
Find similar

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
Oct 30
MIA5:05 amMiami
6h 36m
1 stop
ORD10:41 amChicago O'Hare Intl
Nov 3
ORD11:12 amChicago O'Hare Intl
10h 15m
1 stop
MIA10:27 pmMiami
$126
Find similar
Frontier
Dec 4
MIA9:03 pmMiami
18h 54m
1 stop
ORD2:57 pmChicago O'Hare Intl
Dec 7
ORD6:00 amChicago O'Hare Intl
10h 14m
1 stop
MIA5:14 pmMiami
$129
Find similar
Frontier
Dec 6
MIA5:30 amMiami
17h 54m
1 stop
ORD10:24 pmChicago O'Hare Intl
Jan 14
ORD6:40 amChicago O'Hare Intl
13h 11m
1 stop
MIA8:51 pmMiami
$130
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 October 22, 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

Tue 11/25

8:10 am-10:35 am

Nonstop3h 25m

Chicago O'Hare Intl

Sun 12/7

7:41 pm-11:57 pm

Nonstop3h 16m

$96

MiamiChicago

MIA - ORD

MIAORD

Miami

Thu 12/4

4:08 pm-6:36 pm

Nonstop3h 28m

Chicago O'Hare Intl

Thu 12/11

7:41 pm-11:57 pm

Nonstop3h 16m

$97

MiamiChicago

MIA - ORD

MIAORD

Miami

Fri 1/9

7:09 pm-12:01 am

1 stop5h 52m

Chicago O'Hare Intl

Wed 1/14

1:35 pm-5:50 pm

Nonstop3h 15m

$112

MiamiChicago

MIA - ORD

MIAORD

Miami

Fri 11/7

10:15 pm-10:30 am

1 stop13h 15m

Chicago O'Hare Intl

Mon 11/10

12:17 pm-4:22 pm

Nonstop3h 05m

$113

MiamiChicago

MIA - ORD

MIAORD

Miami

Thu 12/4

9:03 pm-2:57 pm

1 stop18h 54m

Chicago O'Hare Intl

Sun 12/7

6:00 am-5:14 pm

1 stop10h 14m

$129

MiamiChicago

MIA - ORD

MIAORD

Miami

Sat 12/6

5:30 am-10:24 pm

1 stop17h 54m

Chicago O'Hare Intl

Wed 1/14

6:40 am-8:51 pm

1 stop13h 11m

$130

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 2/26

3:56 pm-6:35 pm

Nonstop3h 39m

Chicago O'Hare Intl

Mon 3/2

9:15 am-5:54 pm

1 stop7h 39m

$295

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 2/26

3:56 pm-6:35 pm

Nonstop3h 39m

Chicago O'Hare Intl

Mon 3/2

10:44 am-3:00 pm

Nonstop3h 16m

$349

Key WestChicago

EYW - ORD

EYWORD

Key West

Tue 11/4

2:11 pm-4:51 pm

Nonstop3h 40m

Chicago O'Hare Intl

Sat 11/8

5:00 am-1:27 pm

1 stop7h 27m

$361

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 2/26

4:00 pm-6:36 pm

Nonstop3h 36m

Chicago O'Hare Intl

Mon 3/2

8:00 am-12:22 pm

Nonstop3h 22m

$385

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 $219.

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 $306. 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 $503.

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 $320 when looking at flights departing in the evening. Try not to purchase tickets in the afternoon because they tend to be around $394. 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 $248 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 $180 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.
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  • 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
8,990 reviews
Search United Airlines flights
American AirlinesPriceFrom $289Free CancellationRating
7.2
11,028 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
Schaumburg
Rockford
Merrillville
Gurnee
Naperville
Rosemont
Kenosha
New Buffalo
Joliet
Oak Brook
Orland Park
Racine
Hammond
Tinley Park
Janesville
Elgin
Aurora
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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