RIC - MDW

$96 Find Cheap Flights from Richmond to Chicago Midway Airport

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 Midway departing on 4/23. 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 Midway Airport

 
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

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$290
Overall average: $350
Southwest
Thu 4/23Mon 4/27
RIC - MDW • 1 stop
Cheapest non-stop
$313
Southwest
Fri 5/1Tue 5/5
RIC - MDW • Non-stop
Top airlines
Southwest
Cheapest • from $290 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Every day
You can fly direct with Southwest. Average duration is 2h 05m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top layover airports
Baltimore (BWI)
Cheapest • Avg $404 (round-trip)
Baltimore (BWI)
Shortest trip • 3h 50m (one-way)
Insights
Insights
Insights
Insights
When to travel
February
Cheapest • 58% price drop
June
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Midway!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Richmond to Midway (RIC-MDW)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Richmond to Midway 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 Midway

Thu, Apr 23 - Mon, Apr 27
Southwest Logo
5:35 pm - 10:20 pm
RIC
-
MDW
5h 45m
1 stop
Southwest Logo
2:10 pm - 10:50 pm
MDW
-
RIC
7h 40m
2 stops
$290Southwest
Sat, May 2 - Sat, May 9
Southwest Logo
6:05 am - 12:15 pm
RIC
-
MDW
7h 10m
2 stops
Southwest Logo
12:45 pm - 10:50 pm
MDW
-
RIC
9h 05m
2 stops
$295Southwest
Mon, Apr 20 - Mon, Apr 20
Southwest Logo
6:00 am - 2:55 pm
RIC
-
MDW
9h 55m
2 stops
Southwest Logo
9:30 pm - 11:45 am
MDW
-
RIC
13h 15m
2 stops
$296Southwest
Sat, Apr 18 - Wed, Apr 22
Southwest Logo
6:05 am - 2:40 pm
RIC
-
MDW
9h 35m
2 stops
Southwest Logo
8:00 am - 12:55 pm
MDW
-
RIC
3h 55m
1 stop
$300Southwest
Thu, Apr 16 - Thu, Apr 23
Multiple Airlines Logo
12:20 pm - 7:31 pm
RIC
-
MDW
8h 11m
1 stop
Multiple Airlines Logo
2:15 pm - 7:50 pm
MDW
-
RIC
28h 35m
2 stops
$302Multiple Airlines
Thu, Apr 16 - Thu, Apr 23
Multiple Airlines Logo
12:20 pm - 10:19 pm
RIC
-
MDW
10h 59m
1 stop
Multiple Airlines Logo
2:15 pm - 7:50 pm
MDW
-
RIC
28h 35m
2 stops
$305Multiple Airlines
Fri, May 1 - Tue, May 5
Southwest Logo
7:30 pm - 8:30 pm
RIC
-
MDW
2h 00mnonstop
Southwest Logo
6:00 pm - 8:55 pm
MDW
-
RIC
1h 55mnonstop
$313Southwest
Mon, May 18 - Wed, May 20
Southwest Logo
7:30 pm - 8:30 pm
RIC
-
MDW
2h 00mnonstop
Southwest Logo
12:45 pm - 9:55 pm
MDW
-
RIC
8h 10m
2 stops
$315Southwest
Thu, Apr 23 - Mon, Apr 27
Multiple Airlines Logo
12:20 pm - 7:31 pm
RIC
-
MDW
8h 11m
1 stop
Multiple Airlines Logo
6:00 am - 7:50 pm
MDW
-
RIC
12h 50m
2 stops
$316Multiple Airlines
Tue, Apr 28 - Thu, Apr 30
Southwest Logo
6:50 am - 2:05 pm
RIC
-
MDW
8h 15m
2 stops
Southwest Logo
2:10 pm - 10:50 pm
MDW
-
RIC
7h 40m
2 stops
$317Southwest
Booking Insights

KAYAK's insights & trends for Richmond to Midway flights

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

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

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

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

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Richmond to Chicago Midway Airport, 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 Midway Airport is February, where tickets cost $152 (return) on average. On the other hand, the most expensive months are March and May, where the average cost of round-trip tickets is $497 and $487 respectively.

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

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 $369, prices are generally cheapest when you fly direct.

Find deals

Good to know

Low seasonJanuary
Cheapest flight$96
Best time to beat the crowds with an average 22% drop in price.
Most popular time to fly and prices are also 4% lower on average.
Flight from Richmond to Chicago Midway Airport

When to book flights from Richmond to Midway

Are your dates flexible? Find out the best times to travel from Richmond to Midway 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 Richmond to Chicago Midway Airport flights

  • What is the cheapest flight from Richmond to Chicago Midway Airport?

    In the last 3 days, the lowest price for a flight from Richmond to Chicago Midway Airport was $96 for a one-way ticket and $290 for a round-trip.

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

    No

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

    Richmond and Chicago Midway Airport are both served by 1 main airport. You will leave Richmond from Richmond Byrd Intl and will be arriving at Chicago Midway.

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

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

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

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

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

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

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

    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 Midway Airport.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport 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 Midway Airport?

    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 Midway Airport with an airline and back to Richmond with another airline. Booking your flights between Richmond and MDW can sometimes prove cheaper using this method.

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

    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 Midway Airport 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 Midway Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $183 or less one-way and $379 or less round-trip.

Prefer to fly direct from Richmond to Chicago Midway Airport?

 
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 Midway.
Find which airlines fly direct from Richmond Byrd Intl Airport to Chicago Midway Airport, which days they fly and book direct flights.

Direct departures

Richmond Byrd Intl to Chicago Midway

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

Chicago Midway to Richmond Byrd Intl

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Reviews of the top airline flying from Richmond to Midway

 
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 Midway? 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 4324 reviews
8.6Crew
8.1Boarding
8.0Comfort
7.5Entertainment
7.0Food
Airline reviews

Southwest was greaat! The most expensive but the least upsetting for those we were flying to see.

10.0 ExcellentMartie, Mar 2026
LGB - BNA
Read more Southwest reviews

Southwest was greaat! The most expensive but the least upsetting for those we were flying to see.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

Boarding was easy. The seats are small and fairly uncomfortable

I was supposed to be on a later flight. When I showed up at the gate, the woman working there was extremely helpful getting moved up to this earlier flight.

We had a 5 hour delay on the tarmac in Baltimore

Long layover between flights to Long Island from BWI - need better coordination between flights

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

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

Information on your arrival and departure airports

Richmond (RIC)
Midway (MDW)