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$85+ 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 12/3. Fares are subject to change and may not be available on all flights or dates of travel.
LAX — CHI
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
1 adult, Economy
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Cheapflights Tip: The best prices from Riverside to Chicago are usually found in September or February, booked 56 days in advance, depart on a Thursday or Wednesday and return on a Thursday

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 November 3, 2025.

Most accurate provider

Justfly.com
3 stars

Most trusted provider

Justfly.com
3 stars

Round-trip from

$163
(Kiwi.com)

One-way from

$85
(Mytrip)

Popular in

December

Cheapest in

September

Average price

$323
Provider with most accurate pricing for Los Angeles-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Los Angeles-Chicago (CHI) flights.
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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 ($4 potential savings vs. average RT price).
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Average for round-trip flights in November 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 November 3, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/2. 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 11/216:52 pmLAX - ORD
Nonstop4h 07mMultiple Airlines
Fri 12/59:06 pmORD - LAX
Nonstop4h 46mMultiple Airlines
Deal found 11/2$164
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 12/106:00 amLAX - ORD
1 stop10h 46mMultiple Airlines
Sat 12/139:06 pmORD - LAX
Nonstop4h 46mMultiple Airlines
Deal found 11/2$165
This Mytrip deal was found by Cheapflights users on 11/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/141:20 amLAX - ORD
Nonstop4h 08mSpirit Airlines
Tue 11/184:57 pmORD - LAX
3 stops26h 01mSpirit Airlines
Deal found 11/2$166
This Cheapflightsfares deal was found by Cheapflights users on 11/2. 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 11/2012:19 amLAX - ORD
Nonstop4h 06mSpirit Airlines
Mon 11/244:58 pmORD - LAX
1 stop6h 01mSpirit Airlines
Deal found 11/2$167
This Cheapflightsfares deal was found by Cheapflights users on 11/2. 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 11/249:54 pmLAX - ORD
1 stop5h 38mSpirit Airlines
Thu 11/276:06 pmORD - LAX
Nonstop4h 36mSpirit Airlines
Deal found 11/2$168
This Southwest deal was found by Cheapflights users on 11/1. 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.
Thu 11/276:35 amLAX - MDW
1 stop7h 10mSouthwest
Wed 12/38:55 pmMDW - LAX
Nonstop4h 30mSouthwest
Deal found 11/1$169
This Cheapflightsfares deal was found by Cheapflights users on 11/2. 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.
Sat 12/136:15 amLAX - ORD
1 stop7h 32mSpirit Airlines
Sat 12/139:06 pmORD - LAX
Nonstop4h 46mSpirit Airlines
Deal found 11/2$169
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 12/2412:30 pmLAX - ORD
1 stop9h 42mMultiple Airlines
Tue 12/307:44 pmORD - LAX
Nonstop4h 45mMultiple Airlines
Deal found 11/2$170
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 12/2412:30 pmLAX - ORD
1 stop9h 42mMultiple Airlines
Wed 12/317:44 pmORD - LAX
Nonstop4h 45mMultiple Airlines
Deal found 11/1$171
This Kiwi.com deal was found by Cheapflights users on 11/2. 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.
Thu 12/2511:59 pmLAX - ORD
Nonstop4h 06mSpirit Airlines
Sat 1/37:44 pmORD - LAX
Nonstop4h 45mSpirit Airlines
Deal found 11/2$172
This Cheapflightsfares deal was found by Cheapflights users on 11/2. 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 11/219:54 pmLAX - ORD
1 stop5h 38mSpirit Airlines
Mon 12/18:18 pmORD - LAX
Nonstop4h 39mSpirit Airlines
Deal found 11/2$173
This Cheapflightsfares deal was found by Cheapflights users on 11/1. 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 11/121:20 amLAX - ORD
Nonstop4h 08mSpirit Airlines
Sun 11/169:22 pmORD - LAX
Nonstop4h 37mSpirit Airlines
Deal found 11/1$175

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 November 3, 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 - MDW

LAXMDW

Los Angeles

Thu 11/27

6:35 am-3:45 pm

1 stop7h 10m

Chicago Midway

Wed 12/3

8:55 pm-11:25 pm

Nonstop4h 30m

$169

Los AngelesChicago

LAX - MDW

LAXMDW

Los Angeles

Tue 12/2

6:00 am-12:05 pm

Nonstop4h 05m

Chicago Midway

Wed 12/10

4:15 pm-6:40 pm

Nonstop4h 25m

$179

Los AngelesChicago

LAX - MDW

LAXMDW

Los Angeles

Sat 12/13

2:17 pm-11:47 pm

1 stop7h 30m

Chicago Midway

Tue 12/16

9:34 am-2:31 pm

1 stop6h 57m

$217

Los AngelesChicago

LAX - MDW

LAXMDW

Los Angeles

Mon 12/8

11:40 pm-9:19 am

1 stop7h 39m

Chicago Midway

Tue 12/16

9:34 am-2:31 pm

1 stop6h 57m

$217

Los AngelesChicago

LAX - ORD

LAXORD

Los Angeles

Sat 12/13

5:30 am-2:17 pm

1 stop6h 47m

Chicago O'Hare Intl

Mon 12/15

5:07 pm-10:28 pm

1 stop7h 21m

$217

Los AngelesChicago

LAX - ORD

LAXORD

Los Angeles

Mon 12/8

11:40 pm-8:40 am

1 stop7h 00m

Chicago O'Hare Intl

Wed 12/17

6:00 am-11:13 am

1 stop7h 13m

$217

Los AngelesChicago

LAX - ORD

LAXORD

Los Angeles

Thu 12/11

10:59 pm-8:39 am

1 stop7h 40m

Chicago O'Hare Intl

Tue 12/16

8:50 am-1:11 pm

1 stop6h 21m

$217

Los AngelesChicago

LAX - MDW

LAXMDW

Los Angeles

Tue 12/2

10:59 pm-9:54 am

1 stop8h 55m

Chicago Midway

Wed 12/10

10:49 am-4:42 pm

1 stop7h 53m

$218

Los AngelesChicago

LAX - ORD

LAXORD

Los Angeles

Fri 11/28

6:00 am-12:04 pm

Nonstop4h 04m

Chicago O'Hare Intl

Wed 12/3

8:12 pm-10:55 pm

Nonstop4h 43m

$224

Los AngelesChicago

LAX - MDW

LAXMDW

Los Angeles

Sat 12/13

5:35 am-11:40 am

Nonstop4h 05m

Chicago Midway

Sat 12/13

2:40 pm-6:50 pm

1 stop6h 10m

$228

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

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 October 31, 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, April is the cheapest month in which you can book a flight from Riverside to Chicago (average of $98). Flying from Riverside to Chicago in July is currently the most expensive (average of $148). 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 November 3, 2025.

It’s optimal to fly from Riverside to Chicago in the afternoon. By choosing this option you can save up to 20% on the cost of your flight, compared to a flight at noon.

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 November 2, 2025.

Travelers seeking maximum savings on their Riverside to Chicago flight should consider departing on Wednesday mornings when fares are most often at their lowest. Monday afternoons 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 November 3, 2025.

The most flights from R1V to CHI are scheduled on a Monday (108 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (63 on average).

How much does it cost to fly round-trip from Riverside to Chicago?

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 November 3, 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
4,240 reviews

Overall

8.0

Entertainment

7.5

Food

7.0

Comfort

8.0

Boarding

8.1

Crew

8.6

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
4,240 reviews
Southwest
8.0
Very good
4,240 reviews

Overall

8.0

Entertainment

7.5

Food

7.0

Comfort

8.0

Boarding

8.1

Crew

8.6

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
8,997 reviews
Southwest
8.0
Very good
4,240 reviews

Overall

8.0

Entertainment

7.5

Food

7.0

Comfort

8.0

Boarding

8.1

Crew

8.6

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
11,034 reviews
Southwest
8.0
Very good
4,240 reviews

Overall

8.0

Entertainment

7.5

Food

7.0

Comfort

8.0

Boarding

8.1

Crew

8.6

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
8,120 reviews
Southwest
8.0
Very good
4,240 reviews

Overall

8.0

Entertainment

7.5

Food

7.0

Comfort

8.0

Boarding

8.1

Crew

8.6

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
3,118 reviews
Southwest
8.0
Very good
4,240 reviews

Overall

8.0

Entertainment

7.5

Food

7.0

Comfort

8.0

Boarding

8.1

Crew

8.6

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 04m. Southwest provides one of the quickest options available for as low as $224. The distance from Riverside to Chicago is about 1740 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 Southwest, with whom users have recently found tickets for as low as $90. However, be on the lookout for offers from Spirit Airlines and Frontier, 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 (93%), United Airlines( 91%).

  • What are the cheapest flights from Riverside to Chicago?

    Looking for the cheapest flight from Riverside to Chicago? While on average our users pay $848, our data indicates the cheapest price to be $80. The most popular route (Los Angeles - Chicago O'Hare Intl), is priced around $73.

  • 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, April is the cheapest month in which you can book a flight from Riverside to Chicago (average of $98). Flying from Riverside to Chicago in July is currently the most expensive (average of $148). 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
Porter
Benton Harbor

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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 November 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$89Average$223FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$103Average$209FlexibilityNo cancel feeOn-time65%
Sun Country AirCheapest$130Average$330FlexibilityNo cancel feeOn-time83%
DeltaCheapest$179Average$362FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$179Average$412FlexibilityNo cancel feeOn-time63%
Alaska AirlinesCheapest$190Average$442FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$200Average$394FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$206Average$402FlexibilityNo cancel feeOn-time69%

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