Illinois

$44+ 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 2/1. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — CUN
Jan 21 — Jan 281
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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 December 22, 2025.

Good round-trip deal

$61 or less

Good one-way deal

$28 or less
Price to beat on a round-trip flight from Illinois.
Price to beat on a one-way flight from Illinois.

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 December 22, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/19. 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.
Fri 2/276:40 amORD - JFK
Nonstop2h 24mFrontier
Sun 3/111:03 amJFK - ORD
Nonstop3h 00mFrontier
Deal found 12/19$77
This Frontier deal was found by Cheapflights users on 12/22. 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.
Fri 1/98:35 amORD - JFK
Nonstop2h 24mFrontier
Wed 1/144:24 pmJFK - ORD
Nonstop3h 00mFrontier
Deal found 12/22$79
This Flightnetwork deal was found by Cheapflights users on 12/21. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/98:35 amORD - JFK
Nonstop2h 24mFrontier
Fri 1/164:24 pmJFK - ORD
Nonstop3h 00mFrontier
Deal found 12/21$80
This Kiwi.com deal was found by Cheapflights users on 12/21. 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 1/56:40 amORD - JFK
Nonstop2h 24mFrontier
Wed 1/71:00 pmJFK - ORD
Nonstop2h 57mFrontier
Deal found 12/21$82
This Frontier deal was found by Cheapflights users on 12/21. 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.
Mon 1/56:40 amORD - JFK
Nonstop2h 24mFrontier
Fri 1/91:00 pmJFK - ORD
Nonstop2h 57mFrontier
Deal found 12/21$83
This Frontier deal was found by Cheapflights users on 12/22. 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.
Fri 2/208:38 amORD - DFW
Nonstop2h 58mFrontier
Sun 2/225:01 amDFW - ORD
Nonstop2h 33mFrontier
Deal found 12/22$89
This Super.com deal was found by Cheapflights users on 12/19. 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.
Sun 3/16:40 amORD - JFK
Nonstop2h 24mFrontier
Fri 3/64:29 pmJFK - ORD
Nonstop3h 00mFrontier
Deal found 12/19$89
This Cheapflightsfares deal was found by Cheapflights users on 12/22. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/49:23 amORD - DFW
1 stop14h 35mSpirit Airlines
Wed 2/117:30 amDFW - ORD
1 stop13h 33mSpirit Airlines
Deal found 12/22$90
This Expedia deal was found by Cheapflights users on 12/20. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/37:20 amORD - DFW
1 stop14h 03mSpirit Airlines
Tue 2/107:30 amDFW - ORD
1 stop13h 33mSpirit Airlines
Deal found 12/20$91
This Kiwi.com deal was found by Cheapflights users on 12/20. 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.
Wed 1/147:20 amORD - DFW
1 stop14h 03mMultiple Airlines
Thu 1/159:09 pmDFW - ORD
Nonstop2h 33mMultiple Airlines
Deal found 12/20$92
This CheapOair deal was found by Cheapflights users on 12/22. 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.
Mon 2/27:20 amORD - MCO
1 stop5h 43mSpirit Airlines
Thu 2/53:43 pmMCO - ORD
Nonstop3h 09mSpirit Airlines
Deal found 12/22$92
This Priceline deal was found by Cheapflights users on 12/22. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/710:07 amORD - FLL
1 stop8h 58mMultiple Airlines
Fri 2/138:27 pmFLL - ORD
Nonstop3h 36mMultiple Airlines
Deal found 12/22$93

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 December 22, 2025. In the last 7 days, Cheapflights users made a total of 2,558,603 searches

Fly to

Cancún

Route

Depart

Return

Price

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Fri 1/30

10:48 am-2:38 pm

Nonstop2h 50m

Orlando

Fri 1/30

5:28 pm-7:41 pm

Nonstop3h 13m

$93

ChicagoFort Lauderdale

ORD - FLL

ORDFLL

Chicago O'Hare Intl

Sat 1/17

7:20 am-11:35 am

Nonstop3h 15m

Fort Lauderdale

Sat 1/17

9:25 pm-11:46 pm

Nonstop3h 21m

$94

ChicagoFort Lauderdale

ORD - FLL

ORDFLL

Chicago O'Hare Intl

Tue 1/20

5:15 am-9:22 am

Nonstop3h 07m

Fort Lauderdale

Tue 1/20

9:25 pm-11:46 pm

Nonstop3h 21m

$104

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Mon 1/19

12:44 pm-4:31 pm

Nonstop2h 47m

Orlando

Mon 1/26

5:28 pm-7:41 pm

Nonstop3h 13m

$113

ChicagoFort Lauderdale

ORD - FLL

ORDFLL

Chicago O'Hare Intl

Sat 1/17

5:32 pm-9:40 pm

Nonstop3h 08m

Fort Lauderdale

Tue 1/20

8:54 am-11:22 am

Nonstop3h 28m

$114

ChicagoFort Lauderdale

ORD - FLL

ORDFLL

Chicago O'Hare Intl

Mon 1/19

5:32 pm-9:40 pm

Nonstop3h 08m

Fort Lauderdale

Thu 1/29

7:10 am-11:47 am

1 stop5h 37m

$120

ChicagoFort Lauderdale

ORD - FLL

ORDFLL

Chicago O'Hare Intl

Sun 1/18

8:43 pm-12:59 am

Nonstop3h 16m

Fort Lauderdale

Thu 1/22

12:11 pm-10:42 pm

1 stop11h 31m

$120

ChicagoFort Lauderdale

ORD - FLL

ORDFLL

Chicago O'Hare Intl

Mon 1/12

12:44 pm-8:10 pm

1 stop6h 26m

Fort Lauderdale

Thu 1/15

7:10 am-11:47 am

1 stop5h 37m

$124

ChicagoNew York

ORD - JFK

ORDJFK

Chicago O'Hare Intl

Sat 1/17

2:30 pm-6:04 pm

Nonstop2h 34m

New York John F Kennedy Intl

Wed 1/21

11:20 am-1:14 pm

Nonstop2h 54m

$139

ChicagoNew York

ORD - JFK

ORDJFK

Chicago O'Hare Intl

Wed 1/28

1:57 pm-5:30 pm

Nonstop2h 33m

New York John F Kennedy Intl

Mon 2/2

3:52 pm-5:45 pm

Nonstop2h 53m

$139

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/22

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, January is the cheapest month in which you can book a flight from Illinois (average of $137). Flying from Illinois in July will prove the most costly (average of $217). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.

When is the cheapest time to fly from Illinois?

Use this chart to determine the cheapest time to fly round-trip from Illinois to Cancún. Price data was last updated on December 16, 2024.

Those who are seeking the cheapest fare on flights departing from Illinois would be wise to consider leaving during Wednesday at noon when prices are typically at their lowest. When considering other options, price-conscious travelers should avoid Thursday evenings when fares are usually the most expensive.

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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 December 22, 2025.
  • What is the cheapest airport to fly out of Illinois?

    Chicago O'Hare Intl airport offers the cheapest routes to Belize City, from $51; whereas Chicago Midway airport is typically cheaper if you're flying to Guatemala City, from $58. 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?

    January 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 Fort Lauderdale from $51 round trip
    Fly from Chicago to Miami from $51 round trip
    Fly from Chicago to Orlando from $58 round trip
    Fly from Chicago to Tampa from $58 round trip
    Fly from Chicago to Dallas from $59 round trip

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