RIC - CHI

$115 Find Cheap Flights from Richmond to Chicago - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Richmond to Chicago departing on 9/18. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$284
Typical prices: $294-$452
American Airlines
Wed 9/9Sat 9/12
RIC - ORD • 1 stop
Cheapest non-stop
$305
Southwest
Sat 9/5Tue 9/8
RIC - MDW • Non-stop
Top airlines
Cheapest • from $284 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with American Airlines, Southwest and United Airlines. Average duration is 2h 18m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest • 12% average savings
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $152 (round-trip)
Shortest trip • 3h 45m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 40% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 26% price drop
Most popular
Good to know
Good to know
+1
+1
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Good to know
+1
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Expert advice
Flight Deals

Cheap Flights from Richmond to Chicago (RIC-CHI)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Richmond to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Richmond to Chicago

Wed, Sep 9 - Sat, Sep 12
American Airlines Logo
10:21 am - 4:00 pm
RIC
-
ORD
6h 39m
1 stop
American Airlines Logo
4:37 pm - 7:57 pm
ORD
-
RIC
2h 20mnonstop
$284American Airlines
Wed, Aug 12 - Mon, Aug 17
Southwest Logo
6:15 am - 11:50 am
RIC
-
MDW
6h 35m
2 stops
Southwest Logo
6:15 pm - 9:15 pm
MDW
-
RIC
2h 00mnonstop
$284Southwest
Fri, Aug 14 - Thu, Aug 20
Multiple Airlines Logo
6:47 pm - 8:52 pm
RIC
-
ORD
27h 05m
1 stop
Multiple Airlines Logo
11:01 am - 5:29 pm
ORD
-
RIC
5h 28m
1 stop
$285Multiple Airlines
Mon, Aug 10 - Tue, Aug 11
Delta Logo
6:42 pm - 10:36 pm
RIC
-
MDW
4h 54m
1 stop
Delta Logo
12:46 pm - 6:12 pm
MDW
-
RIC
4h 26m
1 stop
$289Delta
Thu, Aug 20 - Mon, Aug 24
American Airlines Logo
1:34 pm - 7:46 pm
RIC
-
ORD
7h 12m
1 stop
American Airlines Logo
8:54 am - 3:08 pm
ORD
-
RIC
5h 14m
1 stop
$289American Airlines
Mon, Aug 24 - Thu, Aug 27
Southwest Logo
6:30 am - 2:10 pm
RIC
-
MDW
8h 40m
2 stops
Southwest Logo
1:00 pm - 7:10 pm
MDW
-
RIC
5h 10m
1 stop
$294Southwest
Thu, Oct 8 - Sun, Oct 11
Frontier Logo
3:00 pm - 1:16 pm
RIC
-
ORD
23h 16m
1 stop
Frontier Logo
6:05 am - 2:02 pm
ORD
-
RIC
6h 57m
1 stop
$298Frontier
Tue, Sep 15 - Fri, Sep 18
JetBlue Logo
11:35 am - 7:01 pm
RIC
-
ORD
8h 26m
1 stop
JetBlue Logo
9:38 am - 3:48 pm
ORD
-
RIC
5h 10m
1 stop
$299JetBlue
Thu, Aug 20 - Sun, Aug 23
Frontier Logo
12:01 pm - 1:20 pm
RIC
-
ORD
26h 19m
1 stop
Frontier Logo
2:41 pm - 4:31 pm
ORD
-
RIC
24h 50m
1 stop
$303Frontier
Thu, Aug 27 - Sat, Aug 29
Delta Logo
6:00 am - 9:17 am
RIC
-
MDW
4h 17m
1 stop
Delta Logo
6:11 am - 1:06 pm
MDW
-
RIC
5h 55m
1 stop
$308Delta
Booking Insights

KAYAK's insights & trends for Richmond to Chicago flights

Get data-powered insights and trends into flights from Richmond to Chicago to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Richmond to Chicago?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Richmond to Chicago departing in September.

Flight prices are below average for this route right now.

Flights to Chicago from Richmond usually cost between $320 and $473 in September.
The lowest price found in the past 5 days was $284 on American Airlines (Sep 9-Sep 12).

What is the cheapest Richmond to Chicago flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Richmond to Chicago costs $266 on the route between Richmond (RIC) and Chicago O'Hare Intl Airport (ORD). Over the past month, this route was, on average, 12% cheaper than other Richmond-Chicago routes. It is also the most popular route.

What’s the cheapest day of the week to fly from Richmond to Chicago?

The average price of all round-trip flights from Richmond to Chicago clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Chicago on a Saturday and more expensive on a Sunday. On your return trip to Richmond, you should consider flying back on a Saturday, and avoid Mondays for better deals.

What is the cheapest month to fly from Richmond to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Richmond to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Richmond to Chicago is February, where tickets cost $288 (return) on average. On the other hand, the most expensive months are June and July, where the average cost of round-trip tickets is $458 and $450 respectively.

Can I save money by flying with a layover from Richmond to Chicago?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $425, prices are generally cheapest when you fly direct.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Richmond to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Richmond to Chicago, you should book around 4 weeks before departure, which saves you about 40% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 14 weeks before departure.

Expert advice

Expert advice for your flight from Richmond to Chicago

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Stefanie Waldek

Stefanie Waldek

Expert on United Airlines

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Blane Bachelor

Blane Bachelor

Expert on Southwest

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

Good to know

Low season

January

Cheapest flight

$115
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly with an average 23% increase in price.
Flight from Richmond to Chicago O'Hare Airport

When to book flights from Richmond to Chicago

Are your dates flexible? Find out the best times to travel from Richmond to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Richmond to Chicago

  • What is the cheapest flight from Richmond to Chicago?

    In the last 5 days, the lowest price for a flight from Richmond to Chicago was $115 for a one-way ticket and $284 for a round-trip.

  • Do I need a passport to fly between Richmond and Chicago?

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

  • Which airports will I be using when flying from Richmond to Chicago?

    When flying out of Richmond you will be using Richmond Byrd Intl. You will be landing at one of these airports: Chicago Midway or Chicago O'Hare Intl.

  • Which airlines offer Wi-Fi service onboard planes from Richmond to Chicago?

    American Airlines, Delta, JetBlue, and Alaska Airlines offer inflight Wi-Fi service on the Richmond to Chicago flight route.

  • Which aircraft models fly most regularly from Richmond to Chicago?

    The Embraer 175 (Enhanced Winglets) is the aircraft model that flies most regularly on the Richmond to Chicago flight route.

  • Which airline alliances offer flights from Richmond to Chicago?

    SkyTeam, Star Alliance, and oneworld are the airline alliances operating flights between Richmond and Chicago, with SkyTeam being the most commonly used for this route.

  • On which days can I fly direct from Richmond to Chicago?

    There are nonstop flights from Richmond to Chicago on a daily basis.

  • Which is the best airline for flights from Richmond to Chicago, Southwest or United Airlines?

    The two airlines most popular with KAYAK users for flights from Richmond to Chicago are Southwest and United Airlines. With an average price for the route of $353 and an overall rating of 8.0, Southwest is the most popular choice. United Airlines is also a great choice for the route, with an average price of $424 and an overall rating of 7.4.

  • How does KAYAK find such low prices on flights from Richmond to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Richmond to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Richmond to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Richmond is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Richmond to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Richmond with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Richmond to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Richmond up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Richmond to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $235 or less one-way and $402 or less round-trip.

Prefer to fly direct from Richmond to Chicago?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Richmond Byrd Intl to Chicago.
Find which airlines fly direct from Richmond Byrd Intl Airport to Chicago, which days they fly and book direct flights.

Direct departures

Richmond Byrd Intl to Chicago

Monday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Tuesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Wednesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Thursday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Friday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Saturday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Sunday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

See more direct flights

Direct returns

Chicago to Richmond Byrd Intl

Monday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Tuesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Wednesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Thursday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Friday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Saturday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Sunday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

See more direct flights

Reviews of the top 4 airlines serving from Richmond to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Richmond to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Richmond to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4238 reviews
8.0Comfort
7.5Entertainment
7.0Food
8.1Boarding
8.6Crew
Airline reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

2.0 MediocreMatthew, Jun 2026
CVG - MDW
Read more Southwest reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

Great flight. I didn't get a drink because I was asleep whole on the flight.

Love them will get a Southwest card to track my points and keep flying with them. My family and I were pleased with the services.

WiFi was not working and didn’t have a beverage service

The trip was good. Short, uneventful, and can't ask for more than that My one complaint is that I had signed up for wheel chair assist between gates. I fractured my foot/ankle in two places and needed the help. Neither flight did the requested help appear. I ended up walking through both Atlanta and Nashville Airport and was a very unhappy traveler. While I know that it's the airport responsibility for the service, I wish that SW had at least verified that the assistance was there as requested.

I liked that we arrived safely. I did not like how Southwest personnel blamed the boarding delays on wheel chair passengers. If there is a national wheelchair basketball tournament occurring, be ready as a company to respond with appropriate resources to match your cudtomers needs.

I would have preferred a flight voucher and to hop on a different flight. Delayed over 6 hours.

I almost missed my connection in Chicago due to having to wait on a gate to be open I am assuming. Having to run from E terminal to C terminal and I barely made it there before they closed the door. This may not be the actual airline's fault it's crazy how there is so little time between flight especially when they are placed so far apart in the airport.

The Wi-Fi did not work, so you weren't able to watch entertainment on your own device. They did not have wired headphones so you couldn't watch it on the in-seat entertainment screen either. There was plenty of time to do a drink and snag service but the flight attendants chose not to.

Great experience, boarding was fast and efficient, so much so that we arrived to Chicago very early

The flight did not have its customary snacks during the flight. Apparently they were never loaded on the plane.

The seats on this flight weren’t as comfortable as we had expected. Even leaned back these seats left us feeling crappy in our backs. Also we had to use our own tablets for movies, but nothing in the seats in front of us to hold the tablets up.

The head rest is too big and cannot be placed differently/removed. Causes one head to tilt forward and increase back pain

They did the one thing that really matters - got to Chicago early.

It is a modern tragedy that any airline expects you to travel for 14 hours in such discomfort and that the only way to add comfort is exorbitant prices. I was in pain by the time we landed. Shameful.

Planes were on time, we were offered opportunities to take seats in exit aisles that had better leg room, tasks offs and landings were smooth, we were kept informed of flight status

They did not offer coffee on a 7am flight…awful!!

RIC Staff was not enough. Elderly passengers had to wait 30 minutes to deplane, so we could board and still had to walk as no chairs were provided. And, passenger in front of my seat assignment rammed seat against my legs entire flight time. Was mildly bruised and left thigh still sore.

The flight had a delay that made me being in a real rush to take the second flight. The delay was almost for 2 hours. They moved us from gate to gate in 4 times. Once I arrived to Philadelphia, I got to run thorough all the airport, as the train was already closed by that time. So I got sick with asthma for all the running I had to do. And I was the last one to board, when it was almost closed. So irresponsable with the people

5.5 hour delay with no explanation on why, along with no proactive effort to reaccomodate me.

Flight overall was good. Landing was a little rough, but could be attributed to the rainy weather.

The free internet access did not work, so we had to purchase 2 Internet packages. Flight attendants were not proactive in checking in with first class patrons

Equipment swap led to 2+ hour delay on international flight. And to top it off, boarding took forever.

Wretched scheduling - they got themselves into a critical crew situation and didn’t try to address it until 15 minutes before they had to cancel my flight

Terrible. I hate flying with AA. There is always a high level of stress felt when I fly with them.

Biggest issue was original flight canceled and booked to another flight 6 hours earlier and received no notification

The seats were roomier than other airplanes I’ve been on.

The security line at JFK was one of the longest I’ve ever experienced - probably 45 minutes. I don’t know if JetBlue has control over it, but it detracted from the overall experience. Entertainment had good options, but the volume control was a bit small to tap on and the screen had a fair amount of interference blips. Clearer picture would have been better.

I liked the entertainment on JetBlue, the service from JFK to JAX was terrible at best

I usually dont fly JeTBlue and I dont think I will ever do it again. The flight was delayed fee time, nobody was giving us any info at at the airport, gate changing, the slowest and poorly organized boarding ever, rude staff.. huh

The flight was delayed. I upgraded to more room. I can't imagine how small the regular seats are I haven't upgraded for my return flight yet.

Horrible - for the first time in my life i was denied boarding an international flight because the name used on my ticket - Josh - was not exactly the same as my passport - Joshua. At no time during ticketing, online check-in, or at the airport flying from Boston to NY was i notified of a problem. It was only at boarding from NY to Costa Rica I was informed of the problem and by then it was too late. After missing the flight I was told by airport Jet Blue staff, including a supervisor, that it was my problem and they could not assist because i bought "the cheapest fare". i was hung up on twice by JetBlue customer service, including once by a supervisor. I blame Kayak and your awful partner ChatDeal for even allowing me to purchase an international ticket without verifying this - you effectively sold me a ticket i could not use. Shame on you and shame on ChatDeal for doing nothing to help me resolve the situation. What a scam.

Like the variety of entertainment options. One crew member was a little on the rough/rude side. Boarding was a mess, attendants didn't do a great job of helping with the luggage storage and it delayed us a couple of minutes.

The flight kept getting delayed, but the ground crew did not communicate well to the passengers in the terminal. First, we were told that it was an engine issue. That was understandable. We asked, after the third delay, if it would be canceled; they reassured us that that would not happen because a new plane was on its way from Washington DC. Four hours later, that is exactly what happened. No announcement was made only people who had the JetBlue app learned of the cancellation. They rebooked us on a flight that would get into our destination 36 hours after our original time I had to spend an exorbitant amount of money to book an additional flight with a different airline, the following morning in order to make it to my conference in time. Not to mention the fact that by the time I discovered the cancellation on the departures board, it was too late for me to receive a refund on my lodging in the destination city for that night. Because I had booked with KAYAK, I did not receive any JetBlue email with rebooking information. This is what the information information desk kept telling everyone who inquired about a rebooking. This was my first time flying with JetBlue. Needless to say, after extremely poor communication andover $1000 of additional expense later, I will not be flying with them again.

There were mutliple delays. There was inconsistent, delayed, and poor communication regarding the delays.

I volunteered to let them put my carry on suitcase in the baggage storage area. But when we landed I was told it was being unloaded IN A DIFFERENT TERMINAL! I had to walk (painful for me) a long way to retrieve my bag and my ride had to move from the waiting area they were in to a totally different one. Not happy.

Everything you need to know for your flight from Richmond to Chicago

Information on your arrival and departure airports