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$93+ 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 8/25. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — CHI
Jun 30 — Jul 71
Tue 6/30
Tue 7/7
1 adult, Economy
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Cheapflights Tip: The best prices from Richmond Byrd Intl to Chicago are usually found in February or September, booked 89 days in advance, depart on a Saturday or Wednesday and return on a Wednesday

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 May 31, 2026.

This Booking.com deal was found by Cheapflights users on 5/27. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/164:42 pm
RIC
-
ORD
1 stop7h 28m
Frontier
Mon 7/205:13 pm
ORD
-
RIC
1 stop22h 23m
Frontier
Deal found 5/27$307
This Southwest deal was found by Cheapflights users on 5/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/310:50 am
RIC
-
MDW
2 stops8h 25m
Southwest
Tue 9/811:55 am
MDW
-
RIC
Nonstop1h 55m
Southwest
Deal found 5/28$308
This Delta deal was found by Cheapflights users on 5/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/187:15 pm
RIC
-
ORD
1 stop5h 44m
Delta
Mon 9/216:25 pm
ORD
-
RIC
1 stop5h 14m
Delta
Deal found 5/29$309
This Southwest deal was found by Cheapflights users on 5/27. 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.
Sat 10/178:35 am
RIC
-
MDW
Nonstop1h 55m
Southwest
Mon 10/1912:55 pm
MDW
-
RIC
Nonstop1h 55m
Southwest
Deal found 5/27$309
This American Airlines deal was found by Cheapflights users on 5/30. 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.
Wed 7/227:02 am
RIC
-
ORD
Nonstop2h 33m
American Airlines
Sat 7/253:58 pm
ORD
-
RIC
Nonstop2h 16m
American Airlines
Deal found 5/30$310
This Southwest deal was found by Cheapflights users on 5/30. 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.
Tue 6/307:25 am
RIC
-
MDW
Nonstop1h 55m
Southwest
Sat 7/412:45 pm
MDW
-
RIC
Nonstop1h 55m
Southwest
Deal found 5/30$310
This American Airlines deal was found by Cheapflights users on 5/30. 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.
Sat 8/224:02 pm
RIC
-
ORD
1 stop4h 45m
American Airlines
Mon 8/311:15 pm
ORD
-
RIC
1 stop6h 26m
American Airlines
Deal found 5/30$311
This Delta deal was found by Cheapflights users on 5/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/205:42 pm
RIC
-
MDW
1 stop5h 54m
Delta
Mon 8/246:05 am
MDW
-
RIC
1 stop4h 51m
Delta
Deal found 5/29$311
This American Airlines deal was found by Cheapflights users on 5/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/138:01 pm
RIC
-
ORD
Nonstop2h 35m
American Airlines
Wed 7/158:10 am
ORD
-
RIC
Nonstop2h 20m
American Airlines
Deal found 5/28$313
This Southwest deal was found by Cheapflights users on 5/26. 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 7/17:25 am
RIC
-
MDW
Nonstop1h 55m
Southwest
Tue 7/146:10 pm
MDW
-
RIC
Nonstop2h 00m
Southwest
Deal found 5/26$313
This Southwest deal was found by Cheapflights users on 5/27. 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.
Sat 6/276:35 pm
RIC
-
MDW
Nonstop2h 00m
Southwest
Tue 6/3011:50 am
MDW
-
RIC
2 stops9h 25m
Southwest
Deal found 5/27$315
This Southwest deal was found by Cheapflights users on 5/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/204:25 pm
RIC
-
MDW
1 stop5h 35m
Southwest
Mon 8/247:55 am
MDW
-
RIC
2 stops10h 15m
Southwest
Deal found 5/29$316

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 May 31, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$307
(Booking.com)

One-way from

$93
(Delta)

Popular in

May

Cheapest in

February

Average price

$414

Good round-trip deal

$406 or less

Good one-way deal

$223 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. 11% potential increase in price ($46 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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 May 31, 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 - MDW

RICMDW

Richmond Byrd Intl

Sat 9/5

6:30 am-10:40 am

1 stop5h 10m

Chicago Midway

Tue 9/8

10:10 am-8:45 pm

2 stops9h 35m

$328

RichmondChicago

RIC - RFD

RICRFD

Richmond Byrd Intl

Wed 7/15

6:04 pm-10:37 am

2 stops17h 33m

Chicago Greater Rockford

Mon 7/20

8:39 am-8:17 am

1 stop22h 38m

$332

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Tue 6/30

7:25 am-8:20 am

Nonstop1h 55m

Chicago Midway

Wed 7/8

4:10 pm-10:20 pm

1 stop5h 10m

$333

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Tue 6/30

4:55 pm-11:10 pm

2 stops7h 15m

Chicago Midway

Sat 7/11

4:50 pm-11:10 pm

1 stop5h 20m

$335

RichmondChicago

RIC - ORD

RICORD

Richmond Byrd Intl

Tue 9/1

7:00 am-10:58 am

1 stop4h 58m

Chicago O'Hare Intl

Wed 9/2

8:45 am-2:05 pm

1 stop4h 20m

$337

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Thu 9/3

4:25 pm-9:00 pm

1 stop5h 35m

Chicago Midway

Tue 9/8

9:40 am-8:45 pm

2 stops10h 05m

$337

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Tue 6/30

4:55 pm-11:10 pm

2 stops7h 15m

Chicago Midway

Mon 7/13

8:05 pm-11:00 pm

Nonstop1h 55m

$338

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Thu 6/25

7:45 pm-8:40 pm

Nonstop1h 55m

Chicago Midway

Tue 6/30

11:50 am-10:15 pm

2 stops9h 25m

$338

RichmondChicago

RIC - ORD

RICORD

Richmond Byrd Intl

Tue 8/18

8:05 am-2:09 pm

1 stop7h 04m

Chicago O'Hare Intl

Sun 8/23

6:51 am-12:13 pm

1 stop4h 22m

$343

RichmondChicago

RIC - RFD

RICRFD

Richmond Byrd Intl

Wed 7/15

6:04 pm-10:37 am

2 stops17h 33m

Chicago Greater Rockford

Mon 7/27

8:39 am-8:17 am

1 stop22h 38m

$348

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/29

Showing 1-10 of 60 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 May.
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, December is the cheapest month in which you can book a flight from Richmond to Chicago (average of $73). Flying from Richmond to Chicago in April is currently the most expensive (average of $237). 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 May 31, 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 10% 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 May 31, 2026.

The most flights from RIC to CHI are scheduled on a Sunday (30 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (10 on average).

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

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

The best time to book flights from Richmond to Chicago is 89 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 May 30, 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 May 31, 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
4,261 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Walter,May 2026

LAS - BUR

Short but excellent flight. Everyone was friendly and professional it was a great flight!
Southwest
8.0
Very good
4,261 reviews
Southwest
8.0
Very good
4,261 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Walter,May 2026

LAS - BUR

Short but excellent flight. Everyone was friendly and professional it was a great flight!
United Airlines
7.4
Good
9,768 reviews
Southwest
8.0
Very good
4,261 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Walter,May 2026

LAS - BUR

Short but excellent flight. Everyone was friendly and professional it was a great flight!
American Airlines
7.1
Good
11,642 reviews
Southwest
8.0
Very good
4,261 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Walter,May 2026

LAS - BUR

Short but excellent flight. Everyone was friendly and professional it was a great flight!

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 1h 55m. Southwest provides one of the quickest options available for as low as $333. 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, Delta ($98), JetBlue ($126), and Southwest ($178) offers the cheapest pricing from Richmond to Chicago. You may be able to fly from Richmond to Chicago for 71% 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: Japan Airlines (88%), GoJet (87%), Republic Airways( 85%).

  • What are the cheapest flights from Richmond to Chicago?

    Looking for the cheapest flight from Richmond to Chicago? While on average our users pay $1,104, our data indicates the cheapest price to be $187. The most popular route (Richmond Byrd Intl - Chicago O'Hare Intl), is priced around $237.

  • 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, December is the cheapest month in which you can book a flight from Richmond to Chicago (average of $73). Flying from Richmond to Chicago in April is currently the most expensive (average of $237). 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
Hammond
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 May 31, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$98Average$260FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$126Average$352FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$178Average$384FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$223Average$395FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$261Average$430FlexibilityNo cancel feeOn-time69%

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