RIC - CHI

$95 Find Cheap Flights from Richmond to Chicago

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 4/30. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Richmond to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Richmond to Chicago, as well as popular online travel agencies
Travelers love KAYAK
41.299.237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$300
Typical prices: $453-$349
Southwest
Wed 7/1Tue 7/7
RIC - MDW • 1 stop
Cheapest non-stop
$303
Typical prices: $475-$334
American Airlines
Fri 5/15Sat 5/23
RIC - ORD • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
United's Economy Plus offers more legroom than standard.
Southwest provides two free checked bags for flexibility.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $300 (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 31m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest • 1% average savings
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $175 (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 50% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 52% price drop
Most popular
Good to know
Good to know
+1
+1
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+1
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Flight Deals
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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, Jul 1 - Tue, Jul 7
Southwest Logo
4:55 pm - 9:35 pm
RIC
-
MDW
5h 40m
1 stop
Southwest Logo
6:10 pm - 9:05 pm
MDW
-
RIC
1h 55mnonstop
$300Southwest
Mon, May 11 - Wed, May 13
Southwest Logo
5:35 pm - 10:20 pm
RIC
-
MDW
5h 45m
1 stop
Southwest Logo
6:00 pm - 8:55 pm
MDW
-
RIC
1h 55mnonstop
$301Southwest
Tue, May 5 - Thu, May 7
Multiple Airlines Logo
8:39 pm - 12:23 pm
RIC
-
ORD
16h 44m
1 stop
Multiple Airlines Logo
8:59 pm - 4:33 pm
ORD
-
RIC
18h 34m
2 stops
$302Multiple Airlines
Fri, May 8 - Sat, May 9
Spirit Airlines Logo
5:28 pm - 11:15 pm
RIC
-
ORD
6h 47m
1 stop
Spirit Airlines Logo
9:17 am - 4:33 pm
ORD
-
RIC
30h 16m
3 stops
$303Spirit Airlines
Wed, May 6 - Fri, May 8
Multiple Airlines Logo
10:57 am - 9:27 am
RIC
-
ORD
23h 30m
1 stop
Multiple Airlines Logo
1:59 pm - 10:17 am
ORD
-
RIC
19h 18m
2 stops
$304Multiple Airlines
Sat, May 30 - Sat, Jun 20
Southwest Logo
8:10 am - 9:15 am
RIC
-
MDW
2h 05mnonstop
Southwest Logo
6:55 pm - 9:50 pm
MDW
-
RIC
1h 55mnonstop
$304Southwest
Mon, May 11 - Thu, May 14
United Airlines Logo
6:15 am - 7:38 am
RIC
-
ORD
2h 23mnonstop
United Airlines Logo
9:35 pm - 12:51 am
ORD
-
RIC
2h 16mnonstop
$305United Airlines
Thu, May 28 - Sun, May 31
Spirit Airlines Logo
5:28 pm - 10:14 pm
RIC
-
ORD
29h 46m
3 stops
Spirit Airlines Logo
5:05 am - 4:33 pm
ORD
-
RIC
10h 28m
1 stop
$306Spirit Airlines
Thu, May 14 - Wed, May 20
Delta Logo
6:00 am - 8:43 am
RIC
-
MDW
3h 43m
1 stop
Delta Logo
6:23 am - 2:35 pm
MDW
-
RIC
7h 12m
1 stop
$308Delta
Wed, Jun 3 - Sun, Jun 7
United Airlines Logo
6:00 am - 7:23 am
RIC
-
ORD
2h 23mnonstop
United Airlines Logo
6:45 am - 10:01 am
ORD
-
RIC
2h 16mnonstop
$309United Airlines
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 July.

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 $291 on the route between Richmond (RIC) and Chicago Midway Airport (MDW). Over the past month, this route was, on average, 1% cheaper than other Richmond-Chicago routes. The most popular route is between Richmond (RIC) and Chicago O'Hare Intl Airport (ORD).

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 Monday. On your return trip to Richmond, you should consider flying back on a Wednesday, and avoid Tuesdays 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 $163 (return) on average. On the other hand, the most expensive months are October and June, where the average cost of round-trip tickets is $390 and $388 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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at $352 on average.

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 50% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 13 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 seasonJanuary
Cheapest flight$95
Best time to beat the crowds with an average 1% drop in price.
Most popular time to fly with an average 9% 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 3 days, the lowest price for a flight from Richmond to Chicago was $95 for a one-way ticket and $300 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, JetBlue, Delta, 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 Delta?

    The two airlines most popular with KAYAK users for flights from Richmond to Chicago are Southwest and Delta. With an average price for the route of $335 and an overall rating of 8.0, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $272 and an overall rating of 7.9.

  • 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 $224 or less one-way and $396 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 4330 reviews
8.6Crew
7.5Entertainment
8.1Boarding
7.0Food
8.0Comfort
Airline reviews

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

4.0 OkayDavid, Apr 2026
COS - DAL
Read more Southwest reviews

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

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

The seat was not comfortable. 1D. My back was sore all night and the next day.

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

Great flight from Seattle to Phoenix and to Chicago-Midway from Phoenix

The new boarding process was easy and straightforward. Very pleasant.

The flight was okay. The pilots did an amazing job and kept us updated on the flight. The flight attendants were okay. They found time to be chatty with each other rather than focus on the guests. One of the attendants was a little less warm when asking about my bag I had on my lap that I was using during latter part of the mid- flight. Mind you, it was not the departure descent. I’m respectful to each and every attendant, it was the tone in her voice reminding me to place my carryon bag on the floor. I hope to have a better experience next time.

The entire travel day was a disaster from beginning to end. Woke up at two in the morning to make it to San Juan airport in time for a 5:30 am flight to Milwaukee which connected in Baltimore. Massive delays lead to me missing original connection out of Baltimore. Sixteen hours of delays/rebooking/layover time later, arrived in Milwaukee to find that only one of two checked bags made it there (despite the fact that Southwest brought another 737 jet to San Juan to fly us out to our original Baltimore connection—-not squeezed into another booked flight). The flight from Baltimore to Milwaukee was barely half full, so there was no logical reason to ship my bags out of Baltimore on a different flight to Chicago to then ship to Milwaukee. Southwest decided that my bags should not have been on the same connecting flight I WAS ON to Milwaukee, and then proceeded to accidentally leave my larger bag with the important items in Chicago. Terrible logic and support all around. Extremely angered and disappointed with SW. What a clownish operation your company has become!

It was as expected and I was grateful for the wheel chair help and ease of use.

One of the best airlines for fast boarding, on time arrivals, and top notch service!

Very old plane with no inflight entertainment. I purchased the internet pass and it was nearly unusable.

My tray was broken so i had no place to work or eat except my lap. Flight attendant said I would get an email with some credit or miles, it was a complete waste of time as I could only function at about 20% of normal. I have not received anything yet.

Short trip, no food and therefore no expectation for much interaction with staff who were pleasant and professional. My critique is on comfort of the seats. Exit rows and comfort seats do not provide enough personal space for 3 side-by-side seats, especially when in the middle row. Some passengers are not considerate of the middle seat and there should be signs that state something to the effect of: "please consider giving middle seats use of the armrests."

My flight yesterday evening was delayed 3.5 hours with no water or food service. Poor experience

Transparency from pilots, quick boarding and exiting the plane, staff greeted to each and everyone,

Didn't like sitting on the waiting pad for 30 minutes right after departing the gate. If you're going to do that, just don't board so people can still get up and walk around in the terminal. My luggage was damaged by the baggage handlers.

Pilots lied about waiting on “paperwork”. Sat in the plane for over an hour, waiting on some papers to be printed according to the pilot and then all of a sudden he says good news maintenance is finally on their way. Maybe they can fix it before we get our paperwork. Ended up missing my connection in LaGuardia and as a result, had a fly home to Lexington instead of the Louisville airport. Then paid $100 to uber to Louisville since it was midnight by the time I got in. I wish they would just be transparent with passengers sometimes and not try to beat around the bush on why things are delayed.

The WiFi was horrific. I fly delta often and love their (usually reliable and free) WiFi. On this flight it was intermittent and when it did connect was extremely slow. I couldn’t get any work done while I was on the flight which was extremely frustrating. I was also in the exit row seat where there is now immediate seat in front of you, so while the leg room was nice, I couldn’t even watch the TV when the internet wasn’t working. Finally, for the last 20 mins of the flight, the announcement indicator came on the TV screens and took them over, even though no announcement was being made. Really disappointed.

The flight was way too HOT! And the plane did not have any in-flight TV entertainment.

The tray table was broken and the food was terrible.

The flight I was supposed to be on was supposed to take off at 1:50 from State College. It was delayed over and over and over again until somehow I had to rebook on a flight that was supposed to have left State College at 8 am that morning but didn't end up taking off until almost 6 pm. Not only was this completely unacceptable, the "token from United" was a 15 dollar meal voucher that has to be used by today. I would personally like some miles added to my account for this inconvenience. I was in transit for 8 hours from the time I arrive at State College Aiport to when I got home. I was supposed to be home at 3 pm and I returned at 8 pm. Unacceptable. I have not been on an on Time united flight in nearly 5 years.

newer aircraft, ability to connect my headset via blue tooth for entertainment.

Very comfortable flight, snacks and drinks were good, good communication from crew. Could have used a little more information on timing of boarding for group 5

Great flight. Got to watch a movie. Smooth flight and early arrival at ORD.

It was better than excellent. The staff in Mason City were great. The young woman that pushed my wheelchair did more than could be expected of her. She came from India 17 years ago. I don't remember her name.

After arriving in Chicago, we were taxiing for 1.5 hours with infrequent and untruthful updates about the amount of time it would take to arrive at the gate. Minimally, the team could have provided timing expectations that were more truthful, especially one their original expectations were not met.

Every staff member was professional, friendly and courteous. The pizza twist was ok. It was warm but too much dough.

I had a terrible experience. My flight got delayed from Atlanta to Chicago on Monday April 6, 2026, and that led to me missing my next flight to Brussels. United Airlines didn’t provide me with any accommodation for shelter. I had to sleep at the airport in Chicago. The next flight I was put on didn’t leave until the evening hours of Tuesday 4/7/2026.

The flight was officially delayed 3 times, and was actually later than that. Combined, it was a 3 hour delay, but there was no recognition (miles, voucher, etc). The crew seemed stressed. The captain sounded nervous in his announcements. The flight itself was smooth and uneventful.

Just a bad day to fly. Flight was delayed from scheduled 6:50 pm departure to 8:50 pm. Combination of factors mostly related to weather at the destination airport (which is where the incoming flight originated) which delayed the inbound flight over an hour. Once on board, we taxied but had to hold again on the taxiway for 10 minutes or so. We did not get wheels up until after 9 pm. The flight was smooth but about 18 minutes from our destination, we had to hold for several minutes more due to weather at ORD. We finally landed at ORD about 11:08 pm (accounting for the time difference, that was about a 3 hour delay from our scheduled departure time). It felt like we were never going to get to our destination. But the flight crew and attendants were very good. The movie selection onboard was also very nice. Got to watch half of a movie just during our taxi from the gate at ATL due to the delay!

Very good I can’t complain one bit. Thank you American Airlines for making my flight enjoyable and safe!

The staff and service on American Airlines were truly outstanding. I had requested wheelchair assistance for my mother due to her knee issues, and the team went above and beyond every step of the way—from boarding in Boston to our arrival in Chicago. Their care, professionalism, and attentiveness made the entire experience smooth and stress-free. I’m very grateful for the support they provided.

The new planes (American Eagle) are beautiful and especially comfortable. The flight attendants are consistently professional and courteous. And, while it may seem inconsequential, the new liquid tube of coffee creamer—in contrast to the powdered coffee creamer—makes all the difference in a cup of coffee.

I'm not sure American is capable of on-time arrivals and departures. When you land at ORD, you almost always get held on the tarmac because your gate is still occupied. I may have missed my connection, but that ended up up being significantly delayed as well. Once again, I finally got home well after midnight.

Crew at the gate was very crabby and not at all polite. The plane was very hot the entire flight. And the seat cushion was very worn out.

The staff are very, very professional. It's what flying should feel like.

Flight was delayed half hour before boarding, but when I checked flight aware the plane that would Pick us up had a delay of more than an hour. AA should let us know in advance to avoid waiting several hours in the airport

Delays with no explanation. It could have been handled better.

Jill was the flight attendant in first class she was fabulous!! Best flight attendant I have had in years.!! And I fly every other week. Other can learn from her!!

As a first class customer, there was no power the entire flight which limited my ability to work. I find this unacceptable. The first 11 rows on the left side of the plan were out. I was only offered the option to charge my phone which was not the issue because my laptop was out of power. I asked if there was anything that can be done for me, and the answer was, "no". I was not offered any type of compensation for this AA problem which caused me unnecessary stress due to inability to address business issues on an already challenging travel day. Flight attendants tried to reset the power once but that was the extent of their support. Very disappointing for the lack of expected services on a flight. Please contact me with customer focused response to this complaint.

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

Information on your arrival and departure airports