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Illinois

$36+ Cheap flights from Illinois

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/17. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — CUN
Mar 18 — Mar 251
Wed 3/18
Wed 3/25
1 adult, Economy
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What to know about flights from Illinois

Discover essential information about flights departing from Illinois, including flight schedules, destinations, airlines operating at the Illinois airport, and any specific guidelines or requirements for travelers. Please note that the information is based on the most recent updates available. Data last updated February 16, 2026.

Good round-trip deal

$56 or less

Good one-way deal

$43 or less
Price to beat on a round-trip flight from Illinois.
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Price to beat on a one-way flight from Illinois.
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Find flights from Illinois

Cheapest flights from Illinois
Explore the most affordable flight options available from Illinois. Find the lowest fares based on data from user searches, with prices last updated on February 16, 2026.

This deal was found by Cheapflights users on 2/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/236:31 am
ORD
-
JFK
Nonstop2h 29m
Frontier
Sat 4/2511:04 am
JFK
-
ORD
Nonstop2h 56m
Frontier
Deal found 2/14$76
This Frontier deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2612:05 pm
ORD
-
JFK
Nonstop2h 24m
Frontier
Thu 3/54:29 pm
JFK
-
ORD
Nonstop3h 00m
Frontier
Deal found 2/12$78
This Trip.com deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/912:05 pm
ORD
-
JFK
Nonstop2h 24m
Frontier
Sat 3/144:29 pm
JFK
-
ORD
Nonstop3h 00m
Frontier
Deal found 2/12$80
This Kiwi.com deal was found by Cheapflights users on 2/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/99:05 pm
ORD
-
MIA
Nonstop3h 15m
Multiple Airlines
Thu 3/126:00 am
MIA
-
ORD
Nonstop3h 25m
Multiple Airlines
Deal found 2/14$81
This Frontier deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/512:05 pm
ORD
-
JFK
Nonstop2h 24m
Frontier
Mon 3/164:29 pm
JFK
-
ORD
Nonstop3h 00m
Frontier
Deal found 2/11$81
This Frontier deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/193:52 pm
ORD
-
MIA
Nonstop3h 19m
Frontier
Mon 4/203:27 pm
MIA
-
ORD
Nonstop3h 38m
Frontier
Deal found 2/15$82
This Super.com deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1812:05 pm
ORD
-
JFK
Nonstop2h 24m
Frontier
Mon 3/234:29 pm
JFK
-
ORD
Nonstop3h 00m
Frontier
Deal found 2/15$82
This Super.com deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2710:48 am
ORD
-
MIA
Nonstop3h 15m
Frontier
Sat 2/288:00 am
MIA
-
ORD
Nonstop3h 38m
Frontier
Deal found 2/13$83
This Super.com deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1812:05 pm
ORD
-
JFK
Nonstop2h 24m
Frontier
Thu 3/194:29 pm
JFK
-
ORD
Nonstop3h 00m
Frontier
Deal found 2/13$83
This Spirit deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/24:43 pm
ORD
-
FLL
Nonstop3h 09m
Spirit Airlines
Fri 3/68:54 am
FLL
-
ORD
Nonstop3h 28m
Spirit Airlines
Deal found 2/13$84
This CheapOair deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/57:23 pm
ORD
-
MIA
Nonstop3h 16m
Spirit Airlines
Fri 3/136:00 am
MIA
-
ORD
Nonstop3h 25m
Spirit Airlines
Deal found 2/13$84
This Kiwi.com deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/197:06 am
ORD
-
FLL
Nonstop3h 04m
Multiple Airlines
Fri 4/248:19 pm
FLL
-
ORD
Nonstop3h 38m
Multiple Airlines
Deal found 2/13$85

Find flights from Illinois within your budget

 
Find flights departing from Illinois that match your specified budget. Filter results by price range, allowing you to narrow down options and find flights that fit within your financial constraints. Please note that the search results are based on data from user searches, with fares last updated on February 16, 2026. In the last 7 days, Cheapflights users made a total of 2,558,603 searches

Fly to

Cancún

Route

Depart

Return

Price

ChicagoFort Lauderdale

ORD - FLL

ORDFLL

Chicago O'Hare Intl

Sat 4/25

3:15 pm-9:31 pm

1 stop5h 16m

Fort Lauderdale

Sat 5/2

6:39 pm-9:17 pm

Nonstop3h 38m

$94

ChicagoFort Lauderdale

ORD - FLL

ORDFLL

Chicago O'Hare Intl

Sat 5/2

5:34 pm-9:40 pm

Nonstop3h 06m

Fort Lauderdale

Sat 5/9

5:20 pm-7:47 pm

Nonstop3h 27m

$95

ChicagoFort Lauderdale

ORD - FLL

ORDFLL

Chicago O'Hare Intl

Thu 4/16

1:40 pm-9:31 pm

1 stop6h 51m

Fort Lauderdale

Tue 4/21

9:50 pm-12:14 am

Nonstop3h 24m

$102

ChicagoFort Lauderdale

ORD - FLL

ORDFLL

Chicago O'Hare Intl

Thu 4/23

1:40 pm-9:31 pm

1 stop6h 51m

Fort Lauderdale

Tue 4/28

9:50 pm-12:14 am

Nonstop3h 24m

$102

ChicagoFort Lauderdale

ORD - FLL

ORDFLL

Chicago O'Hare Intl

Wed 2/25

5:15 am-9:22 am

Nonstop3h 07m

Fort Lauderdale

Fri 2/27

6:45 pm-9:13 pm

Nonstop3h 28m

$103

ChicagoFort Lauderdale

ORD - FLL

ORDFLL

Chicago O'Hare Intl

Mon 3/16

6:10 pm-10:15 pm

Nonstop3h 05m

Fort Lauderdale

Thu 3/19

7:10 am-11:50 am

1 stop5h 40m

$105

ChicagoFort Lauderdale

ORD - FLL

ORDFLL

Chicago O'Hare Intl

Thu 4/16

7:06 am-11:10 am

Nonstop3h 04m

Fort Lauderdale

Mon 4/20

8:24 am-6:54 pm

1 stop11h 30m

$106

ChicagoDallas

ORD - DFW

ORDDFW

Chicago O'Hare Intl

Wed 4/8

1:39 pm-4:32 pm

Nonstop2h 53m

Dallas/Fort Worth

Sat 4/11

2:48 pm-12:38 am

1 stop9h 50m

$108

ChicagoNew York

ORD - JFK

ORDJFK

Chicago O'Hare Intl

Wed 4/15

4:28 pm-12:59 am

1 stop7h 31m

New York John F Kennedy Intl

Fri 4/17

11:04 am-1:00 pm

Nonstop2h 56m

$108

ChicagoFort Lauderdale

ORD - FLL

ORDFLL

Chicago O'Hare Intl

Sun 3/8

4:43 pm-8:52 pm

Nonstop3h 09m

Fort Lauderdale

Fri 3/13

8:55 pm-11:17 pm

Nonstop3h 22m

$115

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/14

Showing 1-10 of 60 results
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Best time to book a flight from Illinois

Have a flexible travel schedule? Discover the best time to fly from Illinois with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Travel insights for flights from Illinois

Get recent, data-driven insights about flights from Illinois including ideal travel times, pricing trends, and more.

What is the cheapest month to book a flight from Illinois?

Currently, April is the cheapest month in which you can book a flight from Illinois (average of $155). Flying from Illinois in July will prove the most costly (average of $210). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.

Which airlines fly from Illinois?

For flights departing from Illinois check dates and pricing for the following: American Airlines, United Airlines, Spirit Airlines, Frontier, Southwest. These airlines depart to the following popular destinations: Cancún.

United Airlines
United Airlines
From $69
American Airlines
American Airlines
From $91
Frontier
Frontier
From $27
Spirit Airlines
Spirit Airlines
From $35

What is the cheapest place to fly to from Illinois?

The cheapest city to fly to from Illinois is Dallas/Fort Worth, with prices starting at $23. Explore other affordable destinations below.

Dallas/Fort Worth
Dallas/Fort Worth
From $23
Washington, D.C.
Washington, D.C.
From $29
Austin Bergstrom
Austin Bergstrom
From $30
New York
New York
From $33

Browse thousands of different options on Cheapflights for your next trip

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Related info for your journey

Access useful and relevant information related to your journey from Illinois. This can include details such as airport transportation, visa requirements, travel insurance, luggage regulations, and any other information that can ensure a smooth and hassle-free travel experience. Please note that the information is based on general guidance and may need to be verified with official sources. Data last updated February 16, 2026.

  • What is the cheapest airport to fly out of Illinois?

    Chicago O'Hare Intl airport offers the cheapest routes to Belize City, from $53; whereas Chicago Midway airport is typically cheaper if you're flying to Belize City, from $55. It's best to make sure you are flexible on dates to find the cheapest possible flight options for your journey.

  • What is the cheapest month to fly from Illinois?

    April is currently the cheapest month to fly from Illinois. At this moment in time July is the most expensive month. These prices are determined by multiple factors and booking in advance can help keep costs down if your schedule is not as flexible.

  • Where are the cheapest places to fly to from Illinois?

    Check out the cheapest flights from Illinois to embark to:
    Fly from Chicago to New York from $53 round trip
    Fly from Chicago to Fort Lauderdale from $58 round trip
    Fly from Chicago to Fort Myers from $59 round trip
    Fly from Chicago to Miami from $61 round trip
    Fly from Chicago to Dallas from $64 round trip

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