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$49+ Cheap flights from Illinois to Chicago (CHI)

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 10/20. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — CHI
oct. 17 — oct. 241
vie. 10/17
vie. 10/24
1 adult, Economy
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Cheap flight deals from Illinois to Chicago

Keep the following information in mind while searching for Illinois to Chicago flight deals. Data was last updated septiembre 17, 2025.

Round-trip from

$97
(Southwest)

One-way from

$49
(Southwest)

Popular in

July

Cheapest in

January

Average price

$239

Good round-trip deal

$228 or less

Good one-way deal

$99 or less
From Illinois to Chicago (CHI)
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One-way flight from Illinois to Chicago (CHI)
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Highest demand for flights based on searches. 0% potential increase in price ($1 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Illinois to Chicago (CHI).
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Price to beat on a one-way flight from Illinois to Chicago (CHI).
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Find flight deals from Illinois to Chicago

Cheapest flights from Illinois to Chicago
Explore the most affordable flight options available from Illinois to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on septiembre 17, 2025.

This Southwest deal was found by Cheapflights users on 9/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/235:40 amSTL - MDW
Nonstop1h 10mSouthwest
lun. 10/277:40 amMDW - STL
Nonstop1h 10mSouthwest
Deal found 9/17$97
This United Airlines deal was found by Cheapflights users on 9/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/155:00 amSTL - ORD
Nonstop1h 30mUnited Airlines
mié. 10/229:25 amORD - STL
Nonstop1h 24mUnited Airlines
Deal found 9/16$97
This American Airlines deal was found by Cheapflights users on 9/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/237:16 amSTL - ORD
Nonstop1h 27mAmerican Airlines
lun. 10/2710:34 pmORD - STL
Nonstop1h 20mAmerican Airlines
Deal found 9/15$98
This Southwest deal was found by Cheapflights users on 9/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 11/510:15 amSTL - MDW
Nonstop1h 10mSouthwest
sáb. 11/159:45 amMDW - STL
2 stops7h 10mSouthwest
Deal found 9/15$112
This United Airlines deal was found by Cheapflights users on 9/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/165:00 amSTL - ORD
Nonstop1h 30mUnited Airlines
mar. 11/112:21 pmORD - STL
Nonstop1h 26mUnited Airlines
Deal found 9/16$114
This Southwest deal was found by Cheapflights users on 9/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/156:55 amSTL - ORD
1 stop5h 50mSouthwest
mié. 10/227:30 amORD - STL
1 stop7h 15mSouthwest
Deal found 9/16$117
This Southwest deal was found by Cheapflights users on 9/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 10/141:30 pmSTL - ORD
1 stop9h 35mSouthwest
mar. 10/211:30 pmORD - STL
1 stop7h 15mSouthwest
Deal found 9/17$122
This Southwest deal was found by Cheapflights users on 9/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/165:40 amSTL - MDW
Nonstop1h 10mSouthwest
jue. 10/237:40 amMDW - STL
Nonstop1h 10mSouthwest
Deal found 9/16$134
This United Airlines deal was found by Cheapflights users on 9/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/2412:25 pmSTL - ORD
Nonstop1h 25mUnited Airlines
sáb. 11/81:00 pmORD - STL
Nonstop1h 25mUnited Airlines
Deal found 9/16$134
This Priceline deal was found by Cheapflights users on 9/16. 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.
jue. 11/611:07 amSTL - MDW
1 stop7h 32mFrontier
vie. 11/76:15 amMDW - STL
1 stop9h 46mFrontier
Deal found 9/16$143
This Priceline deal was found by Cheapflights users on 9/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 9/294:00 pmSTL - ORD
1 stop8h 10mFrontier
jue. 10/25:10 amORD - STL
1 stop9h 54mFrontier
Deal found 9/15$143
This Frontier deal was found by Cheapflights users on 9/16. 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.
vie. 10/39:32 pmSTL - MDW
1 stop12h 49mFrontier
dom. 10/56:20 amMDW - STL
1 stop8h 44mFrontier
Deal found 9/16$144

Cheapflights Fare Finder

 
Customize your flight search to find flights from Illinois to Chicago 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, Cheapflights users made 2,558,603 searches. Data last updated septiembre 17, 2025.
Use the filters below to find and compare flights from Illinois to Chicago that are best for you.

Fly from

Illinois

Fly to

Chicago

Route

Depart

Return

Price

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

jue. 11/20

7:00 am-8:10 am

Nonstop1h 10m

Chicago Midway

jue. 11/20

11:25 am-12:35 pm

Nonstop1h 10m

$97

St. LouisChicago

STL - ORD

STLORD

Lambert-St Louis

mié. 10/15

5:00 am-6:30 am

Nonstop1h 30m

Chicago O'Hare Intl

mié. 10/22

9:25 am-10:49 am

Nonstop1h 24m

$97

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

jue. 10/23

5:40 am-6:50 am

Nonstop1h 10m

Chicago Midway

lun. 10/27

7:40 am-8:50 am

Nonstop1h 10m

$97

St. LouisChicago

STL - ORD

STLORD

Lambert-St Louis

mié. 10/15

5:00 am-6:30 am

Nonstop1h 30m

Chicago O'Hare Intl

mié. 10/15

1:03 pm-2:27 pm

Nonstop1h 24m

$97

St. LouisChicago

STL - ORD

STLORD

Lambert-St Louis

mié. 10/15

12:25 pm-1:50 pm

Nonstop1h 25m

Chicago O'Hare Intl

jue. 10/16

2:20 pm-3:44 pm

Nonstop1h 24m

$97

St. LouisChicago

STL - ORD

STLORD

Lambert-St Louis

mar. 10/14

6:30 am-8:00 am

Nonstop1h 30m

Chicago O'Hare Intl

mar. 10/21

9:25 am-10:49 am

Nonstop1h 24m

$97

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

lun. 10/20

5:40 am-6:50 am

Nonstop1h 10m

Chicago Midway

lun. 10/20

6:00 pm-9:30 pm

1 stop3h 30m

$107

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

mié. 10/15

6:30 am-7:40 am

Nonstop1h 10m

Chicago Midway

mié. 10/15

10:05 am-3:00 pm

1 stop4h 55m

$107

St. LouisChicago

STL - MDW

STLMDW

Lambert-St Louis

mié. 10/15

4:25 pm-10:25 pm

1 stop6h 00m

Chicago Midway

mié. 10/22

10:15 am-3:50 pm

1 stop5h 35m

$117

St. LouisChicago

STL - ORD

STLORD

Lambert-St Louis

mié. 10/15

6:55 am-12:45 pm

1 stop5h 50m

Chicago O'Hare Intl

mié. 10/22

3:10 pm-10:05 pm

1 stop6h 55m

$117

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

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

Have a flexible travel schedule? Discover the best time to fly to Chicago 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.

Cheapflights Insights

Everything you need to know about your flight from Illinois to Chicago

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

Currently, August is the cheapest month in which you can book a flight from Illinois to Chicago (average of $245). Flying from Illinois to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from IL to CHI?

Find hourly flight availability from Illinois to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated septiembre 17, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Illinois to Chicago as you normally would.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated septiembre 17, 2025.
Get a feel of what it's like to fly with United Airlines, American Airlines, and Contour from Illinois to Chicago by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,926 reviews

Comfort

7.3

Entertainment

7.1

Food

6.6

Boarding

7.7

Crew

8.1

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
United Airlines
7.4
Good
8,926 reviews
United Airlines
7.4
Good
8,926 reviews

Comfort

7.3

Entertainment

7.1

Food

6.6

Boarding

7.7

Crew

8.1

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,926 reviews

Comfort

7.3

Entertainment

7.1

Food

6.6

Boarding

7.7

Crew

8.1

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
Contour
7.2
Good
36 reviews
United Airlines
7.4
Good
8,926 reviews

Comfort

7.3

Entertainment

7.1

Food

6.6

Boarding

7.7

Crew

8.1

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

Related info for your journey

Find useful and relevant information for your journey from Illinois to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Illinois to Chicago?

    Airlines like Southwest, United Airlines, and American Airlines fly from Illinois to Chicago in about 1h 10m. The time it takes to get you to your destination is usually consistent. There are 251 mi between Illinois and Chicago. Most flights are nonstop.

  • What are the cheapest airlines to fly from Illinois to Chicago one-way?

    $49 is the cheapest one-way deal found within the past few days, from Southwest. You may also be able to find cheap deals on United Airlines and American Airlines, with prices starting from $49 and $49, respectively.

  • What are the most popular routes from Illinois to Chicago?

    The most popular flight routes from Illinois to Chicago are Lambert-St Louis - Chicago O'Hare Intl, Lambert-St Louis - Chicago Midway and Moline Quad-City - Chicago O'Hare Intl.

  • Can I find deals for flights from Illinois to Chicago that include hotel bookings?

    Yes. In addition to deals on Illinois to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Illinois to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Illinois to Chicago.

  • Can I find deals for business class flights from Illinois to Chicago?

    Yes. Cheapflights offers flight deals from Illinois to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

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

    Currently, August is the cheapest month in which you can book a flight from Illinois to Chicago (average of $245). Flying from Illinois to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Alternative routes for Illinois to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Illinois to Chicago

Discover the top 2 airlines that operate flights from Illinois to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated septiembre 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$148Average$225FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$179Average$328FlexibilityNo cancel feeOn-time71%

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