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$79+ Cheap flights from Richmond (RIC) 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 9/28. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — CHI
Aug 31 — Sep 71
Mon 8/31
Mon 9/7
1 adult, Economy
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Cheapflights Tip: The best prices from Richmond Byrd Intl to Chicago are usually found in February or January, booked 90 days in advance, depart on a Wednesday or Saturday and return on a Saturday

Cheap flight deals from Richmond to Chicago

Cheapest flights from Richmond to Chicago
Explore the most affordable flight options available from Richmond to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 1, 2026.

This United Airlines deal was found by Cheapflights users on 7/26. 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.
Fri 9/47:55 pm
RIC
-
ORD
1 stop4h 45m
United Airlines
Sun 9/67:30 am
ORD
-
RIC
Nonstop2h 17m
United Airlines
Deal found 7/26$298
This Southwest deal was found by Cheapflights users on 7/26. 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.
Wed 8/196:15 am
RIC
-
MDW
2 stops8h 15m
Southwest
Fri 8/216:15 pm
MDW
-
RIC
Nonstop2h 00m
Southwest
Deal found 7/26$298
This Travelocity deal was found by Cheapflights users on 7/30. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2311:50 am
RIC
-
ORD
1 stop8h 32m
Multiple Airlines
Sun 10/256:05 am
ORD
-
RIC
1 stop6h 57m
Multiple Airlines
Deal found 7/30$300
This Kiwi.com deal was found by Cheapflights users on 7/27. 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 10/147:21 pm
RIC
-
ORD
2 stops21h 05m
Multiple Airlines
Mon 10/194:49 pm
ORD
-
RIC
1 stop20h 13m
Multiple Airlines
Deal found 7/27$301
This CheapOair deal was found by Cheapflights users on 7/29. 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 8/176:47 pm
RIC
-
ORD
1 stop19h 49m
Frontier
Thu 8/202:41 pm
ORD
-
RIC
1 stop24h 50m
Frontier
Deal found 7/29$302
This American Airlines deal was found by Cheapflights users on 7/30. 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.
Fri 9/44:02 pm
RIC
-
ORD
1 stop6h 55m
American Airlines
Mon 9/76:45 am
ORD
-
RIC
1 stop6h 56m
American Airlines
Deal found 7/30$303
This Delta deal was found by Cheapflights users on 7/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/215:42 pm
RIC
-
MDW
1 stop5h 54m
Delta
Tue 8/256:42 pm
MDW
-
RIC
1 stop4h 04m
Delta
Deal found 7/28$303
This United Airlines deal was found by Cheapflights users on 7/30. 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.
Thu 9/36:00 am
RIC
-
ORD
Nonstop2h 23m
United Airlines
Sun 9/67:30 am
ORD
-
RIC
Nonstop2h 17m
United Airlines
Deal found 7/30$305
This Southwest deal was found by Cheapflights users on 7/30. 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.
Wed 9/27:50 am
RIC
-
MDW
Nonstop1h 55m
Southwest
Sun 9/61:40 pm
MDW
-
RIC
Nonstop2h 00m
Southwest
Deal found 7/30$305
This American Airlines deal was found by Cheapflights users on 7/31. 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.
Mon 9/148:27 pm
RIC
-
ORD
Nonstop2h 33m
American Airlines
Mon 9/216:29 am
ORD
-
RIC
1 stop4h 22m
American Airlines
Deal found 7/31$306
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 10/293:00 pm
RIC
-
RFD
1 stop17h 54m
Multiple Airlines
Mon 11/25:55 pm
RFD
-
RIC
1 stop13h 18m
Multiple Airlines
Deal found 7/28$307
This Southwest deal was found by Cheapflights users on 7/27. 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.
Tue 8/183:30 pm
RIC
-
MDW
1 stop6h 15m
Southwest
Fri 8/219:20 am
MDW
-
RIC
2 stops8h 50m
Southwest
Deal found 7/27$308

Find flight deals from Richmond to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Richmond (RIC) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 1, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$298
(United Airlines)

One-way from

$79
(Frontier)

Popular in

June

Cheapest in

February

Average price

$389

Good round-trip deal

$388 or less

Good one-way deal

$244 or less
Provider with most accurate pricing for Richmond Byrd Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Richmond Byrd Intl-Chicago (CHI) flights.
Search Deals
From Richmond Byrd Intl to Chicago (CHI)
Search Deals
One-way flight from Richmond Byrd Intl to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 14% potential increase in price ($62 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2026
Search Deals
Price to beat on a round-trip flight from Richmond Byrd Intl to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Richmond Byrd Intl to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Richmond 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 August 1, 2026.
Use the filters below to find and compare flights from Richmond to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

RichmondChicago

RIC - ORD

RICORD

Richmond Byrd Intl

Fri 9/4

7:55 pm-11:40 pm

1 stop4h 45m

Chicago O'Hare Intl

Sun 9/6

7:30 am-10:47 am

Nonstop2h 17m

$298

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Tue 9/22

6:00 am-9:07 am

1 stop4h 07m

Chicago Midway

Thu 9/24

6:05 am-11:51 am

1 stop4h 46m

$303

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Thu 10/15

12:59 pm-6:00 pm

1 stop6h 01m

Chicago Midway

Fri 10/16

9:29 am-4:04 pm

1 stop5h 35m

$303

RichmondChicago

RIC - ORD

RICORD

Richmond Byrd Intl

Tue 11/17

10:29 am-12:00 pm

Nonstop2h 31m

Chicago O'Hare Intl

Sat 11/21

6:20 pm-9:41 pm

Nonstop2h 21m

$305

RichmondChicago

RIC - ORD

RICORD

Richmond Byrd Intl

Mon 12/14

6:30 am-7:53 am

Nonstop2h 23m

Chicago O'Hare Intl

Sat 12/19

6:20 pm-9:30 pm

Nonstop2h 10m

$305

RichmondChicago

RIC - RFD

RICRFD

Richmond Byrd Intl

Thu 10/29

3:00 pm-7:54 am

1 stop17h 54m

Chicago Greater Rockford

Mon 11/2

5:55 pm-8:13 am

1 stop13h 18m

$307

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Thu 10/8

7:35 pm-8:35 pm

Nonstop2h 00m

Chicago Midway

Sat 10/10

11:25 am-9:20 pm

2 stops8h 55m

$308

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Tue 9/29

6:15 am-1:30 pm

2 stops8h 15m

Chicago Midway

Thu 10/1

2:15 pm-11:50 pm

2 stops8h 35m

$313

RichmondChicago

RIC - ORD

RICORD

Richmond Byrd Intl

Wed 8/19

6:00 am-7:23 am

Nonstop2h 23m

Chicago O'Hare Intl

Thu 8/20

6:15 pm-9:37 pm

Nonstop2h 22m

$317

RichmondChicago

RIC - ORD

RICORD

Richmond Byrd Intl

Thu 8/20

6:00 am-7:23 am

Nonstop2h 23m

Chicago O'Hare Intl

Sat 8/22

9:20 pm-12:43 am

Nonstop2h 23m

$317

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

Showing 1-10 of 49 resultsSorted by cheapest first
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Compare providers for flights from Richmond to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Richmond to Chicago in August.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
CheapfaremartPrice Accuracy-Trust Score*1 star
CheapTicketsDealPrice Accuracy1 starTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Richmond-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Richmond-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Richmond-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Richmond-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Richmond-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Richmond to Chicago

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

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

Currently, February is the cheapest month in which you can book a flight from Richmond to Chicago (average of $288). Flying from Richmond to Chicago in June is currently the most expensive (average of $458). 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 RIC to CHI?

Find hourly flight availability from Richmond 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 August 1, 2026.

A simple way to save on the total cost of your ticket is to fly from Richmond to Chicago at noon. If you’re flexible enough to do this you can expect to save up to 14% on your trip compared to booking a flight in the morning.

Weekly flight availability from Richmond to Chicago

Explore weekly flight availability from Richmond 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 August 1, 2026.

The most flights from RIC to CHI are scheduled on a Friday (28 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (11 on average).

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

Airfare is below average for this route at the moment.
Richmond to Chicago flights typically cost between $337 and $458 in September.
The cheapest round-trip price found within the last 5 days was $298 on United Airlines (Sep 4-Sep 6).

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

The best time to book flights from Richmond to Chicago is 88 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 day to fly from Richmond to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Richmond to Chicago. Price data was last updated on July 25, 2026.

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

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 August 1, 2026.
See what other customers who have flown with Southwest,United Airlines, andAmerican Airlines from Richmond to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,226 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Southwest
8.0
Very good
4,226 reviews
Southwest
8.0
Very good
4,226 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
United Airlines
7.4
Good
10,056 reviews
Southwest
8.0
Very good
4,226 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
American Airlines
7.1
Good
11,845 reviews
Southwest
8.0
Very good
4,226 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
JetBlue
7.1
Good
3,029 reviews
Southwest
8.0
Very good
4,226 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Related info for your journey

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

  • What airport do you fly from for flights from Richmond to Chicago?

    Located just 6.9 mi from the city center, Richmond Byrd Intl is the airport most travelers will use when flying to Chicago from Richmond. Booking flights from Byrd Intl (RIC) to Chicago should be relatively easy as there are 19 daily outbound flights to Chicago from 5 different airlines.

  • How long is the flight from Richmond to Chicago?

    A quick flight from Richmond to Chicago can take about 2h. United Airlines provides one of the quickest options available for as low as $308. Airlines will cover a distance of 628 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Richmond to Chicago round-trip?

    According to our current data, JetBlue ($126), Southwest ($178), and American Airlines ($251) offers the cheapest pricing from Richmond to Chicago. You may be able to fly from Richmond to Chicago for 65% less than the average price by searching for these airlines.

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

    When deciding which route to take from Richmond to Chicago consider Richmond Byrd Intl - Chicago O'Hare Intl, Richmond Byrd Intl - Chicago Midway or Richmond Byrd Intl - Chicago Greater Rockford as they are the most popular.

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

    Before booking your flight to Chicago from Richmond, check out the most reliable airlines to get you to your destination on time: Republic Airways (86%), Japan Airlines (85%), ANA( 83%).

  • What are the cheapest flights from Richmond to Chicago?

    Looking for the cheapest flight from Richmond to Chicago? While on average our users pay $1,600, our data indicates the cheapest price to be $174. The most popular route (Richmond Byrd Intl - Chicago O'Hare Intl), is priced around $208.

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

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

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

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

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

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

    Currently, February is the cheapest month in which you can book a flight from Richmond to Chicago (average of $288). Flying from Richmond to Chicago in June is currently the most expensive (average of $458). 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
Benton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter

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Top 5 airlines flying from Richmond to Chicago

Discover the top 5 airlines that operate flights from Richmond 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 August 1, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$126Average$352FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$178Average$404FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$251Average$406FlexibilityNo cancel feeOn-time71%
DeltaCheapest$260Average$260FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$264Average$439FlexibilityNo cancel feeOn-time69%

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