Latest deals
Insights
FAQs
Price Alerts

Cheap flights from Florida Keys to Chicago from $65

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 5/12. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Florida Keys to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
11:23 am - 10:02 pm
MIA
-
MDW
11h 39m
1 stop
Frontier Logo
3:07 pm - 1:28 pm
MDW
-
MIA
21h 21m
1 stop
$138Frontier
Wed, May 6 - Sat, May 9
Frontier Logo
5:05 am - 6:37 pm
MIA
-
MDW
14h 32m
1 stop
Frontier Logo
7:34 pm - 10:12 am
MDW
-
MIA
13h 38m
1 stop
$140Frontier
Sat, Apr 25 - Sat, May 2
Frontier Logo
12:50 pm - 10:19 pm
MIA
-
MDW
10h 29m
1 stop
Frontier Logo
7:34 pm - 10:12 am
MDW
-
MIA
13h 38m
1 stop
$141Frontier
Thu, Apr 23 - Sat, Apr 25
Frontier Logo
1:10 pm - 7:31 pm
MIA
-
MDW
7h 21m
1 stop
Frontier Logo
2:15 pm - 2:15 pm
MDW
-
MIA
23h 00m
1 stop
$143Frontier
Wed, Apr 29 - Fri, May 1
Frontier Logo
5:22 pm - 10:02 pm
MIA
-
MDW
5h 40m
1 stop
Frontier Logo
3:07 pm - 1:28 pm
MDW
-
MIA
21h 21m
1 stop
$144Frontier
Wed, May 6 - Sat, May 9
Multiple Airlines Logo
4:59 pm - 10:14 pm
MIA
-
MDW
6h 15m
1 stop
Multiple Airlines Logo
12:24 pm - 10:47 pm
MDW
-
MIA
9h 23m
1 stop
$146Multiple Airlines
Sat, May 2 - Tue, May 5
Frontier Logo
5:22 pm - 10:02 pm
MIA
-
MDW
5h 40m
1 stop
Frontier Logo
3:07 pm - 1:28 pm
MDW
-
MIA
21h 21m
1 stop
$147Frontier
Thu, May 7 - Sat, May 9
Delta Logo
6:23 pm - 10:28 pm
EYW
-
MDW
5h 05m
1 stop
Delta Logo
10:59 am - 7:49 pm
MDW
-
EYW
7h 50m
1 stop
$329Delta
Wed, May 6 - Wed, May 13
Delta Logo
6:18 pm - 10:28 pm
EYW
-
MDW
5h 10m
1 stop
Delta Logo
10:41 am - 5:23 pm
MDW
-
EYW
5h 42m
1 stop
$359Delta
Sat, Apr 25 - Tue, Apr 28
Delta Logo
6:18 pm - 10:28 pm
EYW
-
MDW
5h 10m
1 stop
Delta Logo
12:52 pm - 7:40 pm
MDW
-
EYW
5h 48m
1 stop
$409Delta
Sat, Apr 25 - Wed, Apr 29

Frontier flights from Florida Keys to Chicago Midway Airport

Our best Frontier deals on Florida Keys to Chicago Midway Airport flight tickets
Frontier
Apr 11
MIA11:35 amMiami
3h 26m
MDW2:01 pmChicago Midway
Apr 13
MDW6:30 amChicago Midway
3h 10m
MIA10:40 amMiami
$124
Frontier
Apr 11
MIA11:35 amMiami
3h 26m
MDW2:01 pmChicago Midway
Apr 13
MDW6:30 amChicago Midway
3h 10m
MIA10:40 amMiami
$129
Frontier
Apr 11
MIA11:35 amMiami
3h 26m
MDW2:01 pmChicago Midway
Apr 13
MDW6:30 amChicago Midway
3h 10m
MIA10:40 amMiami
$134

Southwest flights from Florida Keys to Chicago Midway Airport

Our best Southwest deals on Florida Keys to Chicago Midway Airport flight tickets
Southwest
May 6
MIA6:40 amMiami
3h 10m
MDW8:50 amChicago Midway
May 12
MDW7:55 amChicago Midway
3h 00m
MIA11:55 amMiami
$157
Southwest
May 6
MIA6:40 amMiami
3h 10m
MDW8:50 amChicago Midway
May 9
MDW2:40 pmChicago Midway
6h 25m
1 stop
MIA10:05 pmMiami
$167
Southwest
May 7
MIA6:05 amMiami
3h 15m
MDW8:20 amChicago Midway
May 9
MDW5:00 amChicago Midway
8h 30m
1 stop
MIA2:30 pmMiami
$177

momondo Fare Finder

 
Customize your flight search to find flights from Florida Keys to Chicago Midway 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 11, 2026.
Use the filters below to find and compare flights from Florida Keys to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MiamiChicago

MIA - MDW

MIAMDW

Miami

Wed 5/6

11:23 am-10:02 pm

1 stop11h 39m

Chicago Midway

Sat 5/9

3:07 pm-1:28 pm

1 stop21h 21m

$138

MiamiChicago

MIA - MDW

MIAMDW

Miami

Sat 4/25

5:05 am-6:37 pm

1 stop14h 32m

Chicago Midway

Sat 5/2

7:34 pm-10:12 am

1 stop13h 38m

$140

MiamiChicago

MIA - MDW

MIAMDW

Miami

Thu 4/23

12:50 pm-10:19 pm

1 stop10h 29m

Chicago Midway

Sat 4/25

7:34 pm-10:12 am

1 stop13h 38m

$141

MiamiChicago

MIA - MDW

MIAMDW

Miami

Wed 4/29

1:10 pm-7:31 pm

1 stop7h 21m

Chicago Midway

Fri 5/1

2:15 pm-2:15 pm

1 stop23h 00m

$143

MiamiChicago

MIA - MDW

MIAMDW

Miami

Wed 5/6

5:22 pm-10:02 pm

1 stop5h 40m

Chicago Midway

Sat 5/9

3:07 pm-1:28 pm

1 stop21h 21m

$144

MiamiChicago

MIA - MDW

MIAMDW

Miami

Sat 5/2

4:59 pm-10:14 pm

1 stop6h 15m

Chicago Midway

Tue 5/5

12:24 pm-10:47 pm

1 stop9h 23m

$146

MiamiChicago

MIA - MDW

MIAMDW

Miami

Thu 5/7

5:22 pm-10:02 pm

1 stop5h 40m

Chicago Midway

Sat 5/9

3:07 pm-1:28 pm

1 stop21h 21m

$147

Key WestChicago

EYW - MDW

EYWMDW

Key West

Wed 5/6

6:23 pm-10:28 pm

1 stop5h 05m

Chicago Midway

Wed 5/13

10:59 am-7:49 pm

1 stop7h 50m

$329
Quickest round-trip

Key WestChicago

EYW - MDW

EYWMDW

Key West

Sat 4/25

6:18 pm-10:28 pm

1 stop5h 10m

Chicago Midway

Tue 4/28

10:41 am-5:23 pm

1 stop5h 42m

$359

Key WestChicago

EYW - MDW

EYWMDW

Key West

Sat 4/25

6:18 pm-10:28 pm

1 stop5h 10m

Chicago Midway

Wed 4/29

12:52 pm-7:40 pm

1 stop5h 48m

$409

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

See travel insights to Chicago from

How to get the cheapest flight ticket from Florida Keys to Chicago Midway 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 Midway Airport?

The month of January is, on average, the cheapest month to fly to Chicago Midway Airport from Florida Keys, with most prices found around $128. If you are unable to visit Chicago Midway Airport during the month of January, then departing from Florida Keys during the month December is also very affordable. Most momondo users find prices during this month for around $128.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Thursday is the cheapest day to fly to Chicago Midway Airport from Florida Keys. The lowest ticket price found for a Thursday departure recently was $190. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. 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 $383.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Florida Keys in the evening is the least expensive time of day to depart. momondo users have found prices as low as $135 when looking at flights departing in the evening. Try not to purchase tickets in the afternoon because they tend to be around $261. Of course, these prices can vary depending on the time of year and what airport you fly to.

Can stopping save me money on Florida Keys to Chicago Midway Airport flights?

No. A direct flight is the cheapest option for a flight between Florida Keys to Chicago Midway Airport.

Cheap Florida Keys to Chicago Midway Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Florida Keys to Chicago Midway Airport

Fastest flight time

3h 05m

Direct flights

Every day
The fastest flight from Florida Keys to Chicago Midway Airport takes 3h 05m
Direct flights go from Florida Keys to Chicago Midway Airport every day.
Search flight deals

Frequently asked questions about flying from Florida Keys to Chicago Midway Airport

  • When did momondo last update prices for flights from Florida Keys to Chicago Midway Airport?

    Prices for flights from Florida Keys to Chicago Midway Airport refresh daily.

  • How many operators does momondo search for flights from Florida Keys to Chicago Midway Airport?

  • How old do you have to be to fly from Florida Keys to Chicago Midway Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Florida Keys to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Florida Keys to Chicago Midway Airport?

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Schererville
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

It is quick and easy to find Florida Keys to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits 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?

Once you have performed a search for Florida Keys to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

Of course. momondo tracks the price of Florida Keys to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

An easier way to manage your Chicago Midway Airport trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Mon 5/11
Mon 5/18
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago