Illinois

$58+ 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 9/14. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — CUN
Jun 21 — Jun 281
We work with more than 300 partners to bring you better travel deals

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 June 16, 2025.

Good round-trip deal

$65 or less

Good one-way deal

$44 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 June 16, 2025.

Wed 7/25:51 amORD - LGA
Nonstop2h 09mSpirit Airlines
Tue 7/86:30 pmLGA - ORD
Nonstop2h 35mSpirit Airlines
Deal found 6/14$118
Thu 9/119:42 amORD - BOS
Nonstop2h 28mJetBlue
Thu 9/114:05 pmBOS - ORD
Nonstop2h 50mJetBlue
Deal found 6/14$120
Mon 8/116:40 amORD - LAX
Nonstop4h 28mSpirit Airlines
Mon 8/1111:20 amLAX - ORD
1 stop8h 10mSpirit Airlines
Deal found 6/14$121
Tue 7/19:28 pmORD - EWR
Nonstop2h 18mSpirit Airlines
Fri 7/45:00 amEWR - ORD
Nonstop2h 37mSpirit Airlines
Deal found 6/14$121
Thu 7/1711:21 amORD - DFW
Nonstop2h 30mSpirit Airlines
Wed 7/302:56 pmDFW - ORD
Nonstop2h 14mSpirit Airlines
Deal found 6/16$122
Wed 7/910:00 amORD - BOS
1 stop12h 03mSpirit Airlines
Tue 7/296:15 amBOS - ORD
1 stop10h 16mSpirit Airlines
Deal found 6/15$123
Tue 8/195:27 pmORD - DFW
Nonstop2h 49mFrontier
Sun 8/249:21 pmDFW - ORD
Nonstop2h 40mFrontier
Deal found 6/14$126
Wed 7/25:38 pmORD - EWR
1 stop6h 06mMultiple Airlines
Fri 7/45:00 amEWR - ORD
Nonstop2h 37mMultiple Airlines
Deal found 6/16$130
Sat 9/132:20 pmORD - DFW
Nonstop2h 48mMultiple Airlines
Fri 10/33:20 pmDFW - ORD
Nonstop2h 30mMultiple Airlines
Deal found 6/14$135
Wed 7/97:17 amORD - BOS
Nonstop2h 23mAmerican Airlines
Tue 7/227:00 amBOS - ORD
Nonstop3h 05mAmerican Airlines
Deal found 6/16$139
Wed 9/32:03 pmORD - LGA
Nonstop2h 12mAmerican Airlines
Sat 9/67:48 pmLGA - ORD
Nonstop2h 33mAmerican Airlines
Deal found 6/16$140
Mon 7/219:56 pmORD - LAS
Nonstop4h 09mMultiple Airlines
Wed 7/2312:34 amLAS - ORD
Nonstop3h 29mMultiple Airlines
Deal found 6/13$140

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 June 16, 2025. In the last 7 days, Cheapflights users made a total of 2,558,603 searches

Fly to

Cancún

Route

Depart

Return

Price

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Wed 7/2

5:51 am-9:00 am

Nonstop2h 09m

New York LaGuardia

Tue 7/8

6:30 pm-8:05 pm

Nonstop2h 35m

$118

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 9/11

9:42 am-1:10 pm

Nonstop2h 28m

Boston Logan Intl

Thu 9/11

4:05 pm-5:55 pm

Nonstop2h 50m

$120

ChicagoLos Angeles

ORD - LAX

ORDLAX

Chicago O'Hare Intl

Mon 8/11

6:40 am-9:08 am

Nonstop4h 28m

Los Angeles

Mon 8/11

11:20 am-9:30 pm

1 stop8h 10m

$121

ChicagoNewark

ORD - EWR

ORDEWR

Chicago O'Hare Intl

Tue 7/1

9:28 pm-12:46 am

Nonstop2h 18m

Newark

Fri 7/4

5:00 am-6:37 am

Nonstop2h 37m

$121

ChicagoDallas

ORD - DFW

ORDDFW

Chicago O'Hare Intl

Thu 7/17

11:21 am-1:51 pm

Nonstop2h 30m

Dallas/Fort Worth

Wed 7/30

2:56 pm-5:10 pm

Nonstop2h 14m

$122

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 7/9

10:00 am-11:03 pm

1 stop12h 03m

Boston Logan Intl

Tue 7/29

6:15 am-3:31 pm

1 stop10h 16m

$123

ChicagoNewark

ORD - EWR

ORDEWR

Chicago O'Hare Intl

Tue 7/1

5:38 pm-12:44 am

1 stop6h 06m

Newark

Tue 7/8

5:00 am-6:37 am

Nonstop2h 37m

$124

ChicagoDallas

ORD - DFW

ORDDFW

Chicago O'Hare Intl

Tue 8/19

5:27 pm-8:16 pm

Nonstop2h 49m

Dallas/Fort Worth

Sun 8/24

9:21 pm-12:01 am

Nonstop2h 40m

$126

ChicagoDallas

ORD - DFW

ORDDFW

Chicago O'Hare Intl

Sat 9/13

2:20 pm-5:08 pm

Nonstop2h 48m

Dallas/Fort Worth

Fri 10/3

3:20 pm-5:50 pm

Nonstop2h 30m

$135

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 7/9

8:05 pm-11:32 pm

Nonstop2h 27m

Boston Logan Intl

Tue 7/15

6:07 am-8:05 am

Nonstop2h 58m

$137

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/14

Showing 1-10 of 60 results
1
2
3
...
6

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, September is the cheapest month in which you can book a flight from Illinois (average of $103). Flying from Illinois in May will prove the most costly (average of $198). 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 October 20, 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 Sunday afternoons when fares are usually the most expensive.

Airline reviews for flights from Illinois

Read reviews and ratings of airlines operating flights from Illinois. Gain insights into the quality of service, in-flight amenities, customer experiences, and overall satisfaction to choose the best airline for your Illinois travel. Please note that the reviews are sourced from user searches and were last updated on June 16, 2025. In the last 7 days, Cheapflights users made a total of 2,558,603 searches.
8.0
Very good

Food

7.3

Overall

8.0

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
8.0
Very good
8.0
Very good

Food

7.3

Overall

8.0

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
8.0
Very good

Food

7.3

Overall

8.0

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
8.0
Very good

Food

7.3

Overall

8.0

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
8.0
Very good

Food

7.3

Overall

8.0

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
8.0
Very good

Food

7.3

Overall

8.0

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 June 16, 2025.
  • What is the cheapest airport to fly out of Illinois?

    Chicago O'Hare Intl airport offers the cheapest routes to Belize City, from $74; whereas Chicago Midway airport is typically cheaper if you're flying to Guatemala City, from $77. 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?

    September is currently the cheapest month to fly from Illinois. At this moment in time May 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 Atlanta from $74 round trip
    Fly from Chicago to Nashville from $77 round trip
    Fly from Chicago to Minneapolis from $77 round trip
    Fly from Chicago to Detroit from $77 round trip
    Fly from Chicago to Pittsburgh from $77 round trip

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.