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Cheap flights from Florida Keys to Chicago from $59

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 3/20. 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

Enter your travel dates to find the best prices.
Frontier Logo
11:13 am - 1:41 pm
MIA
-
MDW
3h 28mnonstop
Frontier Logo
6:00 am - 10:13 am
MDW
-
MIA
3h 13mnonstop
$81Frontier
Thu, Mar 12 - Sun, Mar 15
Frontier Logo
11:13 am - 1:41 pm
MIA
-
MDW
3h 28mnonstop
Frontier Logo
6:00 am - 10:13 am
MDW
-
MIA
3h 13mnonstop
$83Frontier
Fri, Mar 13 - Mon, Mar 16
Frontier Logo
11:13 am - 1:41 pm
MIA
-
MDW
3h 28mnonstop
Frontier Logo
6:00 am - 10:13 am
MDW
-
MIA
3h 13mnonstop
$87Frontier
Fri, Mar 6 - Sun, Mar 8
Frontier Logo
11:13 am - 1:41 pm
MIA
-
MDW
3h 28mnonstop
Frontier Logo
6:00 am - 10:13 am
MDW
-
MIA
3h 13mnonstop
$88Frontier
Fri, Mar 6 - Mon, Mar 9
Frontier Logo
11:28 am - 1:56 pm
MIA
-
MDW
3h 28mnonstop
Frontier Logo
6:00 am - 10:13 am
MDW
-
MIA
3h 13mnonstop
$90Frontier
Thu, Mar 5 - Sun, Mar 8
Frontier Logo
11:13 am - 1:41 pm
MIA
-
MDW
3h 28mnonstop
Frontier Logo
6:00 am - 10:13 am
MDW
-
MIA
3h 13mnonstop
$91Frontier
Sat, Mar 7 - Sun, Mar 8
Frontier Logo
11:13 am - 1:41 pm
MIA
-
MDW
3h 28mnonstop
Frontier Logo
6:00 am - 10:13 am
MDW
-
MIA
3h 13mnonstop
$100Frontier
Sat, Mar 14 - Mon, Mar 16
Frontier Logo
11:13 am - 1:41 pm
MIA
-
MDW
3h 28mnonstop
Frontier Logo
6:00 am - 10:13 am
MDW
-
MIA
3h 13mnonstop
$103Frontier
Fri, Mar 6 - Sun, Mar 8
Delta Logo
6:23 pm - 10:28 pm
EYW
-
MDW
5h 05m
1 stop
Delta Logo
6:00 am - 1:44 pm
MDW
-
EYW
6h 44m
1 stop
$278Delta
Thu, Apr 30 - Sun, May 3
Delta Logo
6:23 pm - 10:28 pm
EYW
-
MDW
5h 05m
1 stop
Delta Logo
6:00 am - 1:44 pm
MDW
-
EYW
6h 44m
1 stop
$316Delta
Thu, Apr 30 - Sun, May 3

Frontier flights from Florida Keys to Chicago Midway Airport

Our best Frontier deals on Florida Keys to Chicago Midway Airport flight tickets
Frontier
Mar 12
MIA11:13 amMiami
3h 28m
MDW1:41 pmChicago Midway
Mar 15
MDW6:00 amChicago Midway
3h 13m
MIA10:13 amMiami
$81
Frontier
Mar 13
MIA11:13 amMiami
3h 28m
MDW1:41 pmChicago Midway
Mar 16
MDW6:00 amChicago Midway
3h 13m
MIA10:13 amMiami
$83
Frontier
Feb 26
MIA11:28 amMiami
3h 28m
MDW1:56 pmChicago Midway
Mar 1
MDW6:15 amChicago Midway
3h 13m
MIA10:28 amMiami
$86

Delta flights from Florida Keys to Chicago Midway Airport

Our best Delta deals on Florida Keys to Chicago Midway Airport flight tickets
Delta
Apr 30
EYW6:23 pmKey West
5h 05m
1 stop
MDW10:28 pmChicago Midway
May 3
MDW6:00 amChicago Midway
6h 44m
1 stop
EYW1:44 pmKey West
$278
Delta
Apr 30
EYW6:23 pmKey West
5h 05m
1 stop
MDW10:28 pmChicago Midway
May 3
MDW6:00 amChicago Midway
6h 44m
1 stop
EYW1:44 pmKey West
$316
Delta
Apr 9
EYW7:30 amKey West
5h 32m
1 stop
MDW12:02 pmChicago Midway
Apr 13
MDW10:41 amChicago Midway
5h 42m
1 stop
EYW5:23 pmKey West
$573

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 February 23, 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

MiamiChicago

MIA - MDW

MIAMDW

Miami

Thu 3/12

11:13 am-1:41 pm

Nonstop3h 28m

Chicago Midway

Sun 3/15

6:00 am-10:13 am

Nonstop3h 13m

$81

MiamiChicago

MIA - MDW

MIAMDW

Miami

Fri 3/13

11:13 am-1:41 pm

Nonstop3h 28m

Chicago Midway

Mon 3/16

6:00 am-10:13 am

Nonstop3h 13m

$83

MiamiChicago

MIA - MDW

MIAMDW

Miami

Fri 3/6

11:13 am-1:41 pm

Nonstop3h 28m

Chicago Midway

Sun 3/8

6:00 am-10:13 am

Nonstop3h 13m

$87

MiamiChicago

MIA - MDW

MIAMDW

Miami

Fri 3/6

11:13 am-1:41 pm

Nonstop3h 28m

Chicago Midway

Mon 3/9

6:00 am-10:13 am

Nonstop3h 13m

$88

MiamiChicago

MIA - MDW

MIAMDW

Miami

Thu 3/5

11:28 am-1:56 pm

Nonstop3h 28m

Chicago Midway

Sun 3/8

6:00 am-10:13 am

Nonstop3h 13m

$90

MiamiChicago

MIA - MDW

MIAMDW

Miami

Sat 3/7

11:13 am-1:41 pm

Nonstop3h 28m

Chicago Midway

Sun 3/8

6:00 am-10:13 am

Nonstop3h 13m

$91

MiamiChicago

MIA - MDW

MIAMDW

Miami

Sat 3/14

11:13 am-1:41 pm

Nonstop3h 28m

Chicago Midway

Mon 3/16

6:00 am-10:13 am

Nonstop3h 13m

$100

MiamiChicago

MIA - MDW

MIAMDW

Miami

Fri 3/6

11:13 am-1:41 pm

Nonstop3h 28m

Chicago Midway

Sun 3/8

6:00 am-10:13 am

Nonstop3h 13m

$103

Key WestChicago

EYW - MDW

EYWMDW

Key West

Thu 4/30

6:23 pm-10:28 pm

1 stop5h 05m

Chicago Midway

Sun 5/3

6:00 am-1:44 pm

1 stop6h 44m

$278

Key WestChicago

EYW - MDW

EYWMDW

Key West

Thu 4/30

6:23 pm-10:28 pm

1 stop5h 05m

Chicago Midway

Sun 5/3

6:00 am-1:44 pm

1 stop6h 44m

$316

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 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 October is, on average, the cheapest month to fly to Chicago Midway Airport from Florida Keys, with most prices found around $89. If you are unable to visit Chicago Midway Airport during the month of October, then departing from Florida Keys during the month January 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, Wednesday is the cheapest day to fly to Chicago Midway Airport from Florida Keys. The lowest ticket price found for a Wednesday departure recently was $198. 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 $427.

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 $138 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $250. 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

  • 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
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
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

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