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$80+ Cheap flights from Riverside, CA 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 10/14. Fares are subject to change and may not be available on all flights or dates of travel.
LAX — CHI
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheapflights Tip: The best prices from Riverside to Chicago are usually found in February or August, booked 56 days in advance, depart on a Wednesday or Thursday and return on a Friday

Cheap flight deals from Riverside to Chicago

Keep the following information in mind while searching for Riverside to Chicago flight deals. Data was last updated September 16, 2025.

Round-trip from

$143
(Gotogate)

One-way from

$80
(Kiwi.com)

Popular in

December

Cheapest in

February

Average price

$279
From Riverside to Chicago (CHI)
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One-way flight from Riverside to Chicago (CHI)
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Highest demand for flights based on searches. 9% potential increase in price ($28 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Riverside to Chicago

Cheapest flights from Riverside to Chicago
Explore the most affordable flight options available from Riverside to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 16, 2025.

This Gotogate deal was found by Cheapflights users on 9/14. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/271:23 pmLAX - ORD
1 stop8h 35mMultiple Airlines
Sat 10/47:09 pmORD - LAX
Nonstop4h 31mMultiple Airlines
Deal found 9/14$143
This Orbitz deal was found by Cheapflights users on 9/14. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/112:05 pmLAX - ORD
Nonstop4h 09mSpirit Airlines
Sat 10/47:09 pmORD - LAX
Nonstop4h 31mSpirit Airlines
Deal found 9/14$144
This Frontier deal was found by Cheapflights users on 9/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/157:00 pmLAX - ORD
1 stop10h 54mFrontier
Mon 11/176:30 amORD - LAX
Nonstop4h 26mFrontier
Deal found 9/14$145
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/24:21 pmLAX - ORD
Nonstop4h 22mFrontier
Sat 10/47:00 amORD - LAX
Nonstop4h 29mFrontier
Deal found 9/14$146
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/89:22 amLAX - ORD
1 stop9h 26mMultiple Airlines
Sat 10/117:25 amORD - LAX
Nonstop4h 26mMultiple Airlines
Deal found 9/15$147
This Frontier deal was found by Cheapflights users on 9/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/274:51 pmLAX - ORD
Nonstop4h 22mFrontier
Sat 10/47:00 amORD - LAX
Nonstop4h 29mFrontier
Deal found 9/14$149
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/64:21 pmLAX - ORD
Nonstop4h 22mFrontier
Tue 10/77:15 amORD - LAX
1 stop7h 04mFrontier
Deal found 9/16$151
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/144:42 pmLAX - ORD
Nonstop4h 18mFrontier
Sat 11/156:30 amORD - LAX
Nonstop4h 26mFrontier
Deal found 9/14$152
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
Sat 9/2712:05 pmLAX - ORD
Nonstop4h 09mSpirit Airlines
Sat 10/412:46 pmORD - LAX
1 stop8h 09mSpirit Airlines
Deal found 9/13$154
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/236:44 amLAX - MDW
1 stop15h 52mFrontier
Mon 10/2712:11 pmMDW - LAX
1 stop14h 14mFrontier
Deal found 9/15$157
This Booking.com 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/136:44 amLAX - MDW
1 stop26h 46mFrontier
Sun 11/1612:30 pmMDW - LAX
1 stop21h 35mFrontier
Deal found 9/15$159
This Flightnetwork 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/309:10 amLAX - MDW
1 stop9h 33mFrontier
Thu 11/612:30 pmMDW - LAX
1 stop21h 35mFrontier
Deal found 9/15$161

Cheapflights Fare Finder

 
Customize your flight search to find flights from Riverside 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 September 16, 2025.
Use the filters below to find and compare flights from Riverside to Chicago that are best for you.

Fly from

Riverside

Fly to

Chicago

Route

Depart

Return

Price

Los AngelesChicago

LAX - ORD

LAXORD

Los Angeles

Wed 10/29

6:00 am-12:10 pm

Nonstop4h 10m

Chicago O'Hare Intl

Sat 11/1

8:48 am-11:30 am

Nonstop4h 42m

$197

Los AngelesChicago

LAX - MDW

LAXMDW

Los Angeles

Wed 10/22

11:00 pm-5:00 am

Nonstop4h 00m

Chicago Midway

Sun 10/26

10:15 pm-12:45 am

Nonstop4h 30m

$215

Los AngelesChicago

LAX - ORD

LAXORD

Los Angeles

Fri 10/17

1:20 pm-7:35 pm

Nonstop4h 15m

Chicago O'Hare Intl

Wed 10/22

6:26 pm-9:01 pm

Nonstop4h 35m

$215

Los AngelesChicago

LAX - ORD

LAXORD

Los Angeles

Sat 11/15

12:25 am-6:29 am

Nonstop4h 04m

Chicago O'Hare Intl

Wed 11/19

2:30 pm-5:09 pm

Nonstop4h 39m

$215

Los AngelesChicago

LAX - ORD

LAXORD

Los Angeles

Tue 11/11

12:25 am-6:29 am

Nonstop4h 04m

Chicago O'Hare Intl

Fri 11/14

7:10 am-9:50 am

Nonstop4h 40m

$215

Los AngelesChicago

LAX - ORD

LAXORD

Los Angeles

Thu 11/6

12:40 pm-6:50 pm

Nonstop4h 10m

Chicago O'Hare Intl

Tue 11/11

2:30 pm-5:09 pm

Nonstop4h 39m

$215

Los AngelesChicago

LAX - MDW

LAXMDW

Los Angeles

Sat 11/15

2:17 pm-11:32 pm

1 stop7h 15m

Chicago Midway

Tue 11/18

1:14 pm-8:27 pm

1 stop9h 13m

$217

Los AngelesChicago

LAX - MDW

LAXMDW

Los Angeles

Wed 10/8

12:45 pm-6:40 pm

Nonstop3h 55m

Chicago Midway

Sat 10/11

4:30 pm-6:55 pm

Nonstop4h 25m

$219

Los AngelesChicago

LAX - MDW

LAXMDW

Los Angeles

Sat 10/18

5:55 am-12:00 pm

Nonstop4h 05m

Chicago Midway

Thu 10/23

6:55 pm-11:25 pm

1 stop6h 30m

$225

Los AngelesChicago

LAX - MDW

LAXMDW

Los Angeles

Fri 11/7

4:15 pm-12:05 am

1 stop5h 50m

Chicago Midway

Tue 11/11

8:55 pm-11:25 pm

Nonstop4h 30m

$225

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

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

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

How far ahead should I book a flight from Riverside to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Riverside to Chicago. Price data was last updated on September 12, 2025.

The best time to book flights from Riverside to Chicago is 56 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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

Currently, August is the cheapest month in which you can book a flight from Riverside to Chicago (average of $245). Flying from Riverside 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 R1V to CHI?

Find hourly flight availability from Riverside 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 September 16, 2025.

When flying from Riverside to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

What is the cheapest day to fly from Riverside to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Riverside to Chicago. Price data was last updated on September 14, 2025.

Travelers seeking maximum savings on their Riverside to Chicago flight should consider departing on Friday afternoons when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Riverside to Chicago

Explore weekly flight availability from Riverside to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated September 16, 2025.

The most flights from R1V to CHI are scheduled on a Friday (129 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (76 on average).

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 September 16, 2025.
Read reviews from past customers who have flown Southwest, United Airlines, and American Airlines from Riverside to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
United Airlines
7.4
Good
8,924 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Spirit Airlines
6.3
Okay
8,019 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Frontier
5.8
Fair
3,174 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

Related info for your journey

Find useful and relevant information for your journey from Riverside 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 Riverside to Chicago?

    A quick flight from Riverside to Chicago can take about 4h. United Airlines provides one of the quickest options available for as low as $215. The distance from Riverside to Chicago is about 1746 mi. This flight may include one or multiple stops.

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

    The cheapest airline one-way is Spirit Airlines, with whom users have recently found tickets for as low as $96. However, be on the lookout for offers from Southwest and United Airlines, as they are both options that can get you from Riverside to Chicago for a low price.

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

    The most popular route from Riverside to Chicago is Los Angeles - Chicago O'Hare Intl. You may also consider Los Angeles - Chicago Midway or Los Angeles - Chicago Greater Rockford.

  • What are the most reliable airlines from Riverside to Chicago?

    Before booking your flight to Chicago from Riverside, check out the most reliable airlines to get you to your destination on time: ITA Airways (100%), Air China (85%), United Airlines( 84%).

  • What are the cheapest flights from Riverside to Chicago?

    Looking for the cheapest flight from Riverside to Chicago? While on average our users pay $820, our data indicates the cheapest price to be $70. The most popular route (Los Angeles - Chicago O'Hare Intl), is priced around $146.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Riverside 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 Riverside to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Riverside to Chicago (average of $245). Flying from Riverside 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 Riverside to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 8 airlines flying from Riverside to Chicago

Discover the top 8 airlines that operate flights from Riverside 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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$91Average$232FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$97Average$209FlexibilityNo cancel feeOn-time65%
Sun Country AirCheapest$130Average$330FlexibilityNo cancel feeOn-time83%
United AirlinesCheapest$149Average$379FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$157Average$424FlexibilityNo cancel feeOn-time63%
Alaska AirlinesCheapest$190Average$431FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$192Average$404FlexibilityNo cancel feeOn-time71%
DeltaCheapest$218Average$395FlexibilityNo cancel feeOn-timeN/A

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