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$63+ 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 1/29. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — CHI
Dec 29 — Jan 51
Mon 12/29
Mon 1/5
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 Wednesday or Saturday and return on a Thursday

Find 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 November 29, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/49:49 pmRIC - ORD
2 stops18h 08mMultiple Airlines
Fri 12/127:20 amORD - RIC
1 stop9h 04mMultiple Airlines
Deal found 11/26$264
This JetBlue deal was found by Cheapflights users on 11/26. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/411:00 amRIC - ORD
1 stop9h 43mJetBlue
Sat 12/1311:25 amORD - RIC
1 stop5h 22mJetBlue
Deal found 11/26$265
This Kiwi.com deal was found by Cheapflights users on 11/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/612:13 pmRIC - ORD
1 stop8h 48mMultiple Airlines
Sun 12/142:36 pmORD - RIC
1 stop25h 48mMultiple Airlines
Deal found 11/26$266
This Kiwi.com deal was found by Cheapflights users on 11/27. 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.
Mon 12/159:49 pmRIC - ORD
1 stop24h 59mSpirit Airlines
Tue 12/307:20 amORD - RIC
1 stop8h 49mSpirit Airlines
Deal found 11/27$267
This Kiwi.com deal was found by Cheapflights users on 11/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/612:13 pmRIC - ORD
1 stop12h 56mSpirit Airlines
Mon 12/157:20 amORD - RIC
1 stop9h 04mSpirit Airlines
Deal found 11/26$268
This Kiwi.com deal was found by Cheapflights users on 11/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/39:01 pmRIC - ORD
2 stops15h 07mSpirit Airlines
Fri 12/127:20 amORD - RIC
1 stop9h 04mSpirit Airlines
Deal found 11/26$269
This JetBlue deal was found by Cheapflights users on 11/26. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1111:00 amRIC - ORD
1 stop9h 43mJetBlue
Fri 12/1211:25 amORD - RIC
1 stop5h 22mJetBlue
Deal found 11/26$270
This Mytrip deal was found by Cheapflights users on 11/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/49:49 pmRIC - ORD
2 stops18h 58mSpirit Airlines
Thu 12/113:26 pmORD - RIC
3 stops24h 58mSpirit Airlines
Deal found 11/27$272
This Kiwi.com deal was found by Cheapflights users on 11/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/49:49 pmRIC - ORD
2 stops18h 08mMultiple Airlines
Sun 12/147:20 amORD - RIC
1 stop9h 04mMultiple Airlines
Deal found 11/26$274
This Kiwi.com deal was found by Cheapflights users on 11/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/612:13 pmRIC - ORD
1 stop8h 48mMultiple Airlines
Thu 12/116:15 amORD - RIC
2 stops10h 09mMultiple Airlines
Deal found 11/26$275
This Kiwi.com deal was found by Cheapflights users on 11/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/312:30 pmRIC - ORD
1 stop8h 57mSpirit Airlines
Wed 12/104:38 pmORD - RIC
2 stops23h 46mSpirit Airlines
Deal found 11/26$276
This Kiwi.com deal was found by Cheapflights users on 11/28. 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 12/119:49 pmRIC - MDW
1 stop25h 50mMultiple Airlines
Sun 12/146:37 pmMDW - RIC
1 stop21h 47mMultiple Airlines
Deal found 11/28$279

Cheap 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 November 29, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$262
(Kiwi.com)

One-way from

$63
(Kiwi.com)

Popular in

November

Cheapest in

February

Average price

$388

Good round-trip deal

$306 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. 6% potential increase in price ($27 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
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 November 29, 2025.
Use the filters below to find and compare flights from Richmond to Chicago that are best for you.

Fly from

Richmond

Fly to

Chicago

Route

Depart

Return

Price

RichmondChicago

RIC - ORD

RICORD

Richmond Byrd Intl

Thu 12/4

11:00 am-7:43 pm

1 stop9h 43m

Chicago O'Hare Intl

Sat 12/13

11:25 am-5:47 pm

1 stop5h 22m

$265

RichmondChicago

RIC - ORD

RICORD

Richmond Byrd Intl

Tue 1/6

10:29 am-12:05 pm

Nonstop2h 36m

Chicago O'Hare Intl

Wed 1/7

10:44 am-1:59 pm

Nonstop2h 15m

$277

RichmondChicago

RIC - ORD

RICORD

Richmond Byrd Intl

Wed 12/31

6:25 am-7:54 am

Nonstop2h 29m

Chicago O'Hare Intl

Thu 1/1

10:49 am-2:01 pm

Nonstop2h 12m

$278

RichmondChicago

RIC - ORD

RICORD

Richmond Byrd Intl

Sat 2/14

10:30 am-12:05 pm

Nonstop2h 35m

Chicago O'Hare Intl

Tue 2/17

10:41 am-1:54 pm

Nonstop2h 13m

$278

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Wed 2/11

4:05 pm-7:00 pm

1 stop3h 55m

Chicago Midway

Sun 2/15

9:50 am-12:45 pm

Nonstop1h 55m

$288

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Fri 2/20

1:15 pm-11:25 pm

2 stops11h 10m

Chicago Midway

Sun 2/22

8:56 pm-12:13 pm

1 stop14h 17m

$292

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Sat 2/14

5:10 pm-10:30 pm

2 stops6h 20m

Chicago Midway

Tue 2/17

9:50 am-12:45 pm

Nonstop1h 55m

$293

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Wed 12/31

5:30 pm-6:35 pm

Nonstop2h 05m

Chicago Midway

Thu 1/8

1:50 pm-4:40 pm

Nonstop1h 50m

$293

RichmondChicago

RIC - ORD

RICORD

Richmond Byrd Intl

Tue 1/13

10:46 am-4:44 pm

1 stop6h 58m

Chicago O'Hare Intl

Tue 1/27

6:50 am-12:07 pm

1 stop4h 17m

$297

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Tue 1/6

5:56 pm-10:07 pm

1 stop5h 11m

Chicago Midway

Wed 1/7

6:45 am-2:40 pm

1 stop6h 55m

$297

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/29

Showing 1-10 of 40 results
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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 November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Richmond-Chicago flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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

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

Use this chart to determine the optimal time to book a round-trip flight from Richmond to Chicago. Price data was last updated on November 21, 2025.

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 month to book a flight from Richmond to Chicago?

Currently, March is the cheapest month in which you can book a flight from Richmond to Chicago (average of $50). Flying from Richmond to Chicago in June is currently the most expensive (average of $132). 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 November 29, 2025.

A simple way to save on the total cost of your ticket is to fly from Richmond to Chicago in the morning. If you’re flexible enough to do this you can expect to save up to 12% on your trip compared to booking a flight at noon.

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 November 29, 2025.

Travelers seeking maximum savings on their Richmond to Chicago flight should consider departing on Wednesday mornings 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.

How much does it cost to fly round-trip from Richmond 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 29, 2025.
See what other customers who have flown with Southwest, Delta, and United 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
4,255 reviews

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
Southwest
8.0
Very good
4,255 reviews
Southwest
8.0
Very good
4,255 reviews

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
Delta
7.9
Good
8,012 reviews
Southwest
8.0
Very good
4,255 reviews

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
United Airlines
7.4
Good
9,058 reviews
Southwest
8.0
Very good
4,255 reviews

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
American Airlines
7.2
Good
11,044 reviews
Southwest
8.0
Very good
4,255 reviews

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
Spirit Airlines
6.3
Okay
8,163 reviews
Southwest
8.0
Very good
4,255 reviews

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.

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 9 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 36m. JetBlue provides one of the quickest options available for as low as $277. Airlines will cover a distance of 641 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, Spirit Airlines ($65), Delta ($108), and Southwest ($181) offers the cheapest pricing from Richmond to Chicago. You may be able to fly from Richmond to Chicago for 81% 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: ANA (90%), Envoy Air (90%), Republic Airways( 88%).

  • What are the cheapest flights from Richmond to Chicago?

    Looking for the cheapest flight from Richmond to Chicago? While on average our users pay $903, our data indicates the cheapest price to be $124. The most popular route (Richmond Byrd Intl - Chicago O'Hare Intl), is priced around $135.

  • 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, March is the cheapest month in which you can book a flight from Richmond to Chicago (average of $50). Flying from Richmond to Chicago in June is currently the most expensive (average of $132). 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
Lansing
Hammond
Porter
Benton Harbor
Merrillville

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Alternative routes for Richmond to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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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 November 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$65Average$195FlexibilityNo cancel feeOn-time65%
DeltaCheapest$108Average$260FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$181Average$360FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$219Average$373FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$230Average$391FlexibilityNo cancel feeOn-time69%

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