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Cheap flights from Florida Keys to Chicago from $64

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 1/17. 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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Find the cheapest flights from Florida Keys to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
12:10 pm - 7:07 pm
MIA
-
MDW
7h 57m1 stop
Frontier Logo
6:15 am - 10:28 am
MDW
-
MIA
3h 13mnonstop
$93Frontier
mié., feb. 25 - dom., mar. 1
Frontier Logo
12:16 pm - 12:02 am
MIA
-
MDW
12h 46m1 stop
Frontier Logo
8:19 pm - 12:28 am
MDW
-
MIA
3h 09mnonstop
$100Frontier
jue., ene. 15 - dom., ene. 18
Frontier Logo
12:10 pm - 7:07 pm
MIA
-
MDW
7h 57m1 stop
Frontier Logo
6:15 am - 10:28 am
MDW
-
MIA
3h 13mnonstop
$104Frontier
mié., feb. 25 - dom., mar. 1
Multiple Airlines Logo
11:38 am - 12:02 am
MIA
-
MDW
13h 24m1 stop
Multiple Airlines Logo
8:19 pm - 12:28 am
MDW
-
MIA
3h 09mnonstop
$107Multiple Airlines
jue., ene. 15 - dom., ene. 18
Frontier Logo
11:43 am - 2:06 pm
MIA
-
MDW
3h 23mnonstop
Frontier Logo
7:20 pm - 11:25 pm
MDW
-
MIA
3h 05mnonstop
$108Frontier
lun., ene. 12 - lun., ene. 19
Multiple Airlines Logo
4:01 pm - 12:02 am
MIA
-
MDW
9h 01m1 stop
Multiple Airlines Logo
8:19 pm - 12:28 am
MDW
-
MIA
3h 09mnonstop
$109Multiple Airlines
jue., ene. 15 - dom., ene. 18
Frontier Logo
4:29 pm - 6:54 pm
MIA
-
MDW
3h 25mnonstop
Frontier Logo
7:20 pm - 11:25 pm
MDW
-
MIA
3h 05mnonstop
$110Frontier
vie., ene. 16 - lun., ene. 19
Delta Logo
6:06 pm - 10:22 pm
EYW
-
MDW
5h 16m1 stop
Delta Logo
6:00 am - 1:48 pm
MDW
-
EYW
6h 48m1 stop
$269Delta
vie., ene. 23 - dom., ene. 25
Delta Logo
6:06 pm - 10:22 pm
EYW
-
MDW
5h 16m1 stop
Delta Logo
10:48 am - 5:11 pm
MDW
-
EYW
5h 23m1 stop
$354Delta
mié., ene. 21 - jue., ene. 29
Delta Logo
7:10 am - 11:59 am
EYW
-
MDW
5h 49m1 stop
Delta Logo
10:48 am - 5:11 pm
MDW
-
EYW
5h 23m1 stop
$378Delta
mié., ene. 21 - jue., ene. 29

Frontier flights from Florida Keys to Chicago Midway Airport

Our best Frontier deals on Florida Keys to Chicago Midway Airport flight tickets
Frontier
Feb 25
MIA12:10 pmMiami
7h 57m
1 stop
MDW7:07 pmChicago Midway
Mar 1
MDW6:15 amChicago Midway
3h 13m
MIA10:28 amMiami
$93
Find similar
Frontier
Jan 15
MIA12:16 pmMiami
12h 46m
1 stop
MDW12:02 amChicago Midway
Jan 18
MDW8:19 pmChicago Midway
3h 09m
MIA12:28 amMiami
$100
Find similar
Frontier
Dec 24
MIA12:10 pmMiami
3h 27m
MDW2:37 pmChicago Midway
Jan 7
MDW3:01 pmChicago Midway
3h 10m
MIA7:11 pmMiami
$103
Find similar

Southwest flights from Florida Keys to Chicago Midway Airport

Our best Southwest deals on Florida Keys to Chicago Midway Airport flight tickets
Southwest
Jan 22
MIA2:35 pmMiami
3h 15m
MDW4:50 pmChicago Midway
Jan 26
MDW5:30 pmChicago Midway
3h 00m
MIA9:30 pmMiami
$157
Find similar
Southwest
Jan 22
MIA2:35 pmMiami
3h 15m
MDW4:50 pmChicago Midway
Jan 26
MDW5:30 pmChicago Midway
3h 00m
MIA9:30 pmMiami
$168
Find similar
Southwest
Jan 22
MIA2:35 pmMiami
3h 15m
MDW4:50 pmChicago Midway
Jan 26
MDW5:30 pmChicago Midway
3h 00m
MIA9:30 pmMiami
$177
Find similar

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 diciembre 23, 2025.
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

mié. 2/25

12:10 pm-7:07 pm

1 stop7h 57m

Chicago Midway

dom. 3/1

6:15 am-10:28 am

Nonstop3h 13m

$93

MiamiChicago

MIA - MDW

MIAMDW

Miami

jue. 1/15

12:16 pm-12:02 am

1 stop12h 46m

Chicago Midway

dom. 1/18

8:19 pm-12:28 am

Nonstop3h 09m

$100

MiamiChicago

MIA - MDW

MIAMDW

Miami

mié. 2/25

12:10 pm-7:07 pm

1 stop7h 57m

Chicago Midway

dom. 3/1

6:15 am-10:28 am

Nonstop3h 13m

$104

MiamiChicago

MIA - MDW

MIAMDW

Miami

jue. 1/15

11:38 am-12:02 am

1 stop13h 24m

Chicago Midway

dom. 1/18

8:19 pm-12:28 am

Nonstop3h 09m

$107

MiamiChicago

MIA - MDW

MIAMDW

Miami

lun. 1/12

11:43 am-2:06 pm

Nonstop3h 23m

Chicago Midway

lun. 1/19

7:20 pm-11:25 pm

Nonstop3h 05m

$108

MiamiChicago

MIA - MDW

MIAMDW

Miami

jue. 1/15

4:01 pm-12:02 am

1 stop9h 01m

Chicago Midway

dom. 1/18

8:19 pm-12:28 am

Nonstop3h 09m

$109

MiamiChicago

MIA - MDW

MIAMDW

Miami

vie. 1/16

4:29 pm-6:54 pm

Nonstop3h 25m

Chicago Midway

lun. 1/19

7:20 pm-11:25 pm

Nonstop3h 05m

$110

Key WestChicago

EYW - MDW

EYWMDW

Key West

vie. 1/23

6:06 pm-10:22 pm

1 stop5h 16m

Chicago Midway

dom. 1/25

6:00 am-1:48 pm

1 stop6h 48m

$269

Key WestChicago

EYW - MDW

EYWMDW

Key West

mié. 1/21

6:06 pm-10:22 pm

1 stop5h 16m

Chicago Midway

jue. 1/29

10:48 am-5:11 pm

1 stop5h 23m

$354

Key WestChicago

EYW - MDW

EYWMDW

Key West

mié. 1/21

7:10 am-11:59 am

1 stop5h 49m

Chicago Midway

jue. 1/29

10:48 am-5:11 pm

1 stop5h 23m

$378

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, Friday is the cheapest day to fly to Chicago Midway Airport from Florida Keys. The lowest ticket price found for a Friday departure recently was $195. 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 $308.

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 $137 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $241. 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 10m

Direct flights

Every day
The fastest flight from Florida Keys to Chicago Midway Airport takes 3h 10m
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
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.

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