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Cheap flights from Florida Keys to Illinois from $57

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 Illinois departing on 10/3. 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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Find the cheapest flights from Florida Keys to Illinois

Cheap round-trip flights

Spirit Airlines Logo
7:00 am - 9:22 amMIA-ORD
3h 22mnonstop
Spirit Airlines Logo
10:27 am - 2:29 pmORD-MIA
3h 02mnonstop
$107Spirit Airlines
Find Deal
vie., oct. 10 - dom., oct. 12
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
dom., oct. 19 - vie., oct. 31
Frontier Logo
7:20 am - 9:33 amMIA-MDW
3h 13mnonstop
Frontier Logo
2:05 pm - 6:05 pmMDW-MIA
3h 00mnonstop
$109Frontier
Find Deal
lun., oct. 20 - sáb., nov. 1
Frontier Logo
9:00 am - 11:17 amMIA-MDW
3h 17mnonstop
Frontier Logo
12:17 pm - 4:18 pmMDW-MIA
3h 01mnonstop
$110Frontier
Find Deal
vie., oct. 24 - lun., oct. 27
Multiple Airlines Logo
7:00 am - 9:22 amMIA-ORD
3h 22mnonstop
Multiple Airlines Logo
5:50 pm - 12:34 amORD-MIA
5h 44m1 stop
$111Multiple Airlines
Find Deal
jue., oct. 16 - jue., oct. 23
American Airlines Logo
6:35 am - 8:53 amMIA-ORD
3h 18mnonstop
American Airlines Logo
3:00 pm - 6:59 pmORD-MIA
2h 59mnonstop
$157American Airlines
Find Deal
mié., oct. 22 - sáb., oct. 25
American Airlines Logo
9:40 pm - 11:58 pmMIA-ORD
3h 18mnonstop
American Airlines Logo
8:06 am - 12:12 pmORD-MIA
3h 06mnonstop
$158American Airlines
Find Deal
vie., oct. 24 - lun., oct. 27
Southwest Logo
11:50 am - 1:55 pmMIA-MDW
3h 05mnonstop
Southwest Logo
8:10 am - 12:10 pmMDW-MIA
3h 00mnonstop
$167Southwest
Find Deal
jue., oct. 16 - lun., oct. 20
United Airlines Logo
7:00 am - 12:39 pmMIA-PIA
6h 39m1 stop
United Airlines Logo
10:51 am - 6:17 pmPIA-MIA
6h 26m1 stop
$259United Airlines
Find Deal
vie., nov. 14 - dom., nov. 16
United Airlines Logo
3:12 pm - 11:30 pmEYW-ORD
9h 18m1 stop
United Airlines Logo
11:00 am - 3:19 pmORD-EYW
3h 19mnonstop
$325United Airlines
Find Deal
vie., oct. 24 - lun., oct. 27

American Airlines flights from Florida Keys to Illinois

Our best American Airlines deals on Florida Keys to Illinois flight tickets
American Airlines
Oct 22
MIA6:35 amMiami
3h 18m
ORD8:53 amChicago O'Hare Intl
Oct 25
ORD3:00 pmChicago O'Hare Intl
2h 59m
MIA6:59 pmMiami
$157
Find similar
American Airlines
Oct 24
MIA9:40 pmMiami
3h 18m
ORD11:58 pmChicago O'Hare Intl
Oct 27
ORD8:06 amChicago O'Hare Intl
3h 06m
MIA12:12 pmMiami
$158
Find similar
American Airlines
Oct 14
MIA10:01 pmMiami
2h 55m
STL11:56 pmLambert-St Louis
Oct 21
STL5:23 amLambert-St Louis
2h 47m
MIA9:10 amMiami
$169
Find similar

Spirit Airlines flights from Florida Keys to Illinois

Our best Spirit Airlines deals on Florida Keys to Illinois flight tickets
Spirit Airlines
Oct 1
MIA7:00 amMiami
3h 18m
ORD9:18 amChicago O'Hare Intl
Oct 6
ORD10:27 amChicago O'Hare Intl
3h 02m
MIA2:29 pmMiami
$107
Find similar
Spirit Airlines
Oct 19
MIA7:00 amMiami
3h 22m
ORD9:22 amChicago O'Hare Intl
Oct 31
ORD10:27 amChicago O'Hare Intl
3h 02m
MIA2:29 pmMiami
$109
Find similar
Spirit Airlines
Oct 4
MIA7:00 amMiami
3h 18m
ORD9:18 amChicago O'Hare Intl
Oct 12
ORD10:27 amChicago O'Hare Intl
3h 02m
MIA2:29 pmMiami
$112
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Florida Keys to Illinois 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 18, 2025.
Use the filters below to find and compare flights from Florida Keys to Illinois that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

MiamiChicago

MIA - ORD

MIAORD

Miami

vie. 10/10

7:00 am-9:22 am

Nonstop3h 22m

Chicago O'Hare Intl

dom. 10/12

10:27 am-2:29 pm

Nonstop3h 02m

$107

MiamiChicago

MIA - ORD

MIAORD

Miami

dom. 10/19

7:00 am-9:22 am

Nonstop3h 22m

Chicago O'Hare Intl

vie. 10/31

10:27 am-2:29 pm

Nonstop3h 02m

$109

MiamiChicago

MIA - MDW

MIAMDW

Miami

lun. 10/20

7:20 am-9:33 am

Nonstop3h 13m

Chicago Midway

sáb. 11/1

2:05 pm-6:05 pm

Nonstop3h 00m

$109

MiamiChicago

MIA - MDW

MIAMDW

Miami

vie. 10/24

9:00 am-11:17 am

Nonstop3h 17m

Chicago Midway

lun. 10/27

12:17 pm-4:18 pm

Nonstop3h 01m

$110

MiamiChicago

MIA - ORD

MIAORD

Miami

jue. 10/16

7:00 am-9:22 am

Nonstop3h 22m

Chicago O'Hare Intl

jue. 10/23

5:50 pm-12:34 am

1 stop5h 44m

$111

MiamiChicago

MIA - ORD

MIAORD

Miami

mié. 10/22

6:35 am-8:53 am

Nonstop3h 18m

Chicago O'Hare Intl

sáb. 10/25

3:00 pm-6:59 pm

Nonstop2h 59m

$157

MiamiChicago

MIA - ORD

MIAORD

Miami

vie. 10/24

9:40 pm-11:58 pm

Nonstop3h 18m

Chicago O'Hare Intl

lun. 10/27

8:06 am-12:12 pm

Nonstop3h 06m

$158

MiamiChicago

MIA - MDW

MIAMDW

Miami

jue. 10/16

11:50 am-1:55 pm

Nonstop3h 05m

Chicago Midway

lun. 10/20

8:10 am-12:10 pm

Nonstop3h 00m

$167

MiamiPeoria

MIA - PIA

MIAPIA

Miami

vie. 11/14

7:00 am-12:39 pm

1 stop6h 39m

Greater Peoria

dom. 11/16

10:51 am-6:17 pm

1 stop6h 26m

$259

Key WestChicago

EYW - ORD

EYWORD

Key West

vie. 10/24

3:12 pm-11:30 pm

1 stop9h 18m

Chicago O'Hare Intl

lun. 10/27

11:00 am-3:19 pm

Nonstop3h 19m

$325

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 Illinois from

How to get the cheapest flight ticket from Florida Keys to Illinois

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 Illinois?

The cheapest month to fly to Illinois from Florida Keys is in February. Flight prices, which tend to average around $160, are often lower during this time because this is during the off-season. If you aren’t able to travel to Illinois during the month of February, then flying in September is also cheap. Prices for this month can be found on momondo for an average of $195.

What is the cheapest day to depart on your flight to Illinois?

The cheapest day to depart from Florida Keys to Illinois is on a Thursday when prices can be found for as low as $343. Flights from Florida Keys to Illinois on a Sunday will generally be more expensive and average around $939. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to Illinois?

Our most recent data shows that the best time of day to fly to Illinois is at noon. Flights from Florida Keys to Illinois during this time can be as low as $359. Flights in the morning are often more expensive with an average ticket price of $507.

What is the cheapest Florida Keys to Illinois flight route?

Fly from Key West to Chicago O'Hare Intl for the best Florida Keys - Illinois flight prices

How far in advance should I book a flight to Illinois?

You are more likely to see cheaper flights to Illinois from Florida Keys when booking weeks ahead of your departure date. In general, you can expect to find flights to Illinois for around $248 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Illinois from Florida Keys for as low as $197 on momondo.

What cabin class options are available on Florida Keys to Illinois flights?

There are 4 cabin classes available to choose from on Florida Keys to Illinois 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 Illinois flights?

No. A direct flight is the cheapest option for a flight between Florida Keys to Illinois.

Cheap Florida Keys to Illinois flight deals and tips

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

Fastest flight time

2h 50m

Direct flights

Every day

Airports in Illinois

2 airports
The fastest flight from Florida Keys to Illinois takes 2h 50m
Direct flights go from Florida Keys to Illinois every day.
There are 2 airports near Illinois: Chicago Midway (MDW), Lambert-St Louis (STL)
Search flight deals

  • When did momondo last update prices for flights from Florida Keys to Illinois?

    Prices for flights from Florida Keys to Illinois are refreshed on a daily basis.

  • How many operators does momondo search for flights from Florida Keys to Illinois?

  • How old do you have to be to fly from Florida Keys to Illinois?

    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 Illinois.

  • What documentation or ID do you need to fly to Illinois?

    The required travel and health documents for your Illinois trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Illinois. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Florida Keys to Illinois?

Best airlines flying from Florida Keys to Illinois

Compare and see reviews for airlines that fly from Florida Keys to Illinois with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $224Free CancellationRating
7.4
8,926 reviews
Search United Airlines flights
American AirlinesPriceFrom $259Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Illinois from Florida Keys.

Can I find flights from Florida Keys to Illinois with flexible booking policies on momondo?

Yes. All flights to Illinois from Florida Keys on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Florida Keys to Illinois?

Once all potential Florida Keys to Illinois flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

Yes. momondo can track prices for Florida Keys to Illinois flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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