Cheap Flights from Richmond to Chicago Midway from $411

Compare Richmond to Chicago Midway flight deals

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Flight deals from Richmond Airport to Chicago Midway Airport

Looking for a cheap last-minute deal or the best return flight from Richmond Airport to Chicago Midway Airport? If you want to travel next month, return fares start from $411. Find the lowest prices on one-way and return tickets right here.

Chicago.$411 per passenger.Departing Sat, 18 Apr, returning Mon, 20 Apr.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Richmond on Sat, 18 Apr, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 20 Apr, arriving in Richmond.Price includes taxes and charges.From $411, select.

Chicago.$452 per passenger.Departing Sat, 9 May, returning Mon, 11 May.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Richmond on Sat, 9 May, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 11 May, arriving in Richmond.Price includes taxes and charges.From $452, select.

Chicago.$498 per passenger.Departing Sat, 6 Jun, returning Sun, 7 Jun.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Richmond on Sat, 6 Jun, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sun, 7 Jun, arriving in Richmond.Price includes taxes and charges.From $498, select.

Chicago.$567 per passenger.Departing Thu, 6 Aug, returning Sat, 15 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Richmond on Thu, 6 Aug, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 15 Aug, arriving in Richmond.Price includes taxes and charges.From $567, select.

Chicago.$615 per passenger.Departing Mon, 30 Mar, returning Thu, 2 Apr.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Richmond on Mon, 30 Mar, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 2 Apr, arriving in Richmond.Price includes taxes and charges.From $615, select.

Chicago.$625 per passenger.Departing Thu, 30 Jul, returning Mon, 3 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Richmond on Thu, 30 Jul, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 3 Aug, arriving in Richmond.Price includes taxes and charges.From $625, select.

Chicago.$642 per passenger.Departing Thu, 3 Sep, returning Tue, 8 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Richmond on Thu, 3 Sep, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 8 Sep, arriving in Richmond.Price includes taxes and charges.From $642, select.

Chicago.$645 per passenger.Departing Fri, 17 Jul, returning Sun, 19 Jul.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Richmond on Fri, 17 Jul, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sun, 19 Jul, arriving in Richmond.Price includes taxes and charges.From $645, select.

Chicago.$718 per passenger.Departing Tue, 24 Mar, returning Sat, 28 Mar.Return flight with Delta.Outbound indirect flight with Delta, departs from Richmond on Tue, 24 Mar, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Sat, 28 Mar, arriving in Richmond.Price includes taxes and charges.From $718, select.

Chicago.$753 per passenger.Departing Fri, 9 Oct, returning Mon, 12 Oct.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Richmond on Fri, 9 Oct, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Mon, 12 Oct, arriving in Richmond.Price includes taxes and charges.From $753, select.

Chicago.$754 per passenger.Departing Mon, 23 Mar, returning Thu, 26 Mar.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Richmond on Mon, 23 Mar, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 26 Mar, arriving in Richmond.Price includes taxes and charges.From $754, select.

Find the cheapest month to fly from Richmond to Chicago Midway

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Richmond to Chicago Midway flights are currently cheapest in April.

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Direct flights from Richmond to Chicago Midway

Richmond to Chicago Midway: Alternative routes

Compare routes from Richmond to Chicago below. You may find an airport to fly into that's cheaper, faster, or easier than Chicago Midway.

Richmond to Chicago: Flight information

The things to know before you go.

Cheapest flight found	$411
Cheapest month to fly	April
Average flight time	2 hrs, 1 min
Most popular airline	Southwest Airlines
Average flights per week	10

Finding cheap flights from Richmond to Chicago Midway: Frequently asked questions

How much are return flights from Richmond to Chicago Midway?

The best price we found for a return flight from Richmond to Chicago Midway is $411. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.

How long does it take to fly from Richmond to Chicago Midway?

2 hours and 1 minute is the average flight time from Richmond to Chicago Midway.

Which airlines fly direct from Richmond to Chicago Midway?

Southwest Airlines flies direct from Richmond to Chicago Midway.

How many flights are there a week from Richmond to Chicago Midway?

As of March 2026, there are 10 flights per week flying from Richmond to Chicago Midway.

When is the cheapest time to fly from Richmond to Chicago Midway?

The cheapest month to fly from Richmond to Chicago Midway is usually April.

Which upcoming date is cheapest to fly from Richmond Airport to Chicago Midway Airport on?

After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Richmond Airport to Chicago Midway Airport on Saturday, 18 April 2026.

Can I get a direct flight from Richmond Airport to Chicago Midway Airport?

Yes – the average flight time is 2 hours and 1 minute.

How can I find the best flight deal to Chicago Midway?

We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago Midway but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

When is the best time to book flights to Chicago?

We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.

Which is the cheapest airline to fly from Richmond Airport to Chicago Midway with?

Currently, Southwest Airlines offers the cheapest flight tickets to Chicago Midway.

Travelling from Richmond International Airport (Byrd Field) (RIC) to Chicago Midway International Airport (MDW): what you need to know

The average length of a direct flight from Richmond International Airport (Byrd Field) to Chicago Midway International Airport is 2 hours 5 minutes.
Chicago is one hour behind Richmond and follows the UTC-5 timezone.
You can choose from 11 weekly Richmond International Airport (Byrd Field) to Chicago Midway International Airport flights. The 05:30 departure with Southwest Airlines is the earliest you can take. Southwest Airlines operates the last service of the day at 20:55.
To ensure you get on your RIC to MDW flight, allow plenty of time to check in and find your gate. Turning up two hours ahead of international departures and an hour before domestic flights is the standard rule.
You can expect longer lines during popular months like August. Arriving up to four hours ahead of international flights and two hours for domestic departures will help ensure a smooth travel experience.
Southwest Airlines offers direct flights from Richmond International Airport (Byrd Field) to Chicago Midway International Airport. Book with this popular airline, then get ready to discover the sights in Chicago — and maybe even more of United States if time allows.
The airline that tops the list for bookings on this route is Southwest Airlines.
The most punctual carrier that operates RIC to MDW flights is Southwest Airlines. Its services arrive as planned 70.0% of the time.
If you want to add a stop to your trip, simply deselect 'Direct flights only' when searching for your ticket from Richmond International Airport (Byrd Field) to Chicago Midway International Airport. Here are the most popular stopovers between RIC and MDW:
- Detroit Metropolitan Wayne County Airport
- Philadelphia International Airport
- Baltimore/Wash International Thurgood Marshall Airport

How to find the cheapest flights from Richmond International Airport (Byrd Field) (RIC) to Chicago Midway International Airport (MDW)

$226 is currently the lowest price for a one-way Richmond International Airport (Byrd Field) to Chicago Midway International Airport flight. A return flight starts at $411. These fares can change depending on availability and demand.
Get cheap tickets from RIC to MDW by booking eight months ahead. Based on our research, that's the sweet spot for finding a bargain.
July is the cheapest month for flights from Richmond International Airport (Byrd Field) to Chicago Midway International Airport. If you want to fly during a different time of year, the 'Whole month' tool will show you the lowest airfares for each month.
There's no need to check every day to see if fares have gone down when you create a Price Alert. We'll let you know as soon as there's a new deal on cheap flights from RIC to MDW.
Lock in the perfect flight for you with the help of the filters. To see the 'Cheapest,' 'Best' or 'Fastest' flights from Richmond International Airport (Byrd Field) to Chicago Midway International Airport, use the 'Sort by' tool. You can also filter results by arrival and departure times, airline, and journey duration.

Handy information about Richmond International Airport (Byrd Field) (RIC)

You'll find RIC at 1 Richard E. Byrd Terminal Drive.
When it comes to Richmond International Airport (Byrd Field)'s on-time performance, data shows 77.63% of flights stick to their scheduled arrival time.
Central Richmond to Richmond International Airport (Byrd Field) is approximately 21 kilometres. Depending on traffic, it'll take about 20 minutes to get there if you're ride-sharing, catching a cab or driving.
Expect a journey time of about 2 hours 50 minutes on public transport.
Booked an early flight from Richmond International Airport (Byrd Field) to Chicago Midway International Airport? Avoid the last-minute rush to the airport (and catch some extra z's) by choosing one of these hotels close to RIC:

Arriving at Chicago Midway International Airport (MDW)

If you're arriving on a late Richmond International Airport (Byrd Field) to Chicago Midway International Airport flight, few things top the convenience of staying near the terminal. Grab your bags from the carousel and then be showered and relaxing shortly after at one of these hotels near MDW:
Begin your adventure by picking up a Chicago Midway International Airport rental car. Grab your wheels from Dollar, Hertz or Budget and explore beyond Chicago's main sights.
Lock in the best possible rate by booking your ride from Chicago Midway International Airport around four weeks before your travel date.

Getting from Chicago Midway International Airport (MDW) to central Chicago

You'll find MDW at 5700 South Cicero.
Chicago Midway International Airport is approximately 19 kilometres from central Chicago. The drive time takes about 20 minutes.
If you're using public transport, expect a journey of around 45 minutes.

When to fly to Chicago Midway International Airport (MDW)

The quietest month for a flight from Richmond International Airport (Byrd Field) to Chicago Midway International Airport is May, while July is the most popular. Choose the best time to go to Chicago based on whether you prefer a bustling atmosphere or a more laid-back vibe.
The warmest month in Chicago is July, with temperatures ranging between 15ºC and 29ºC. Book your flights from Richmond International Airport (Byrd Field) to Chicago Midway International Airport in this month if this is the type of weather you like.
Look for cheap tickets from RIC to MDW in January if you'd rather travel during cooler conditions. Temperatures are at their lowest around then, ranging between -12ºC and 3ºC on average.

Explore more of United States

Columbus is just one of the many places in United States waiting to be explored once you've seen Chicago. Around 451 kilometres away to the south-east, well-known attractions include Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.
Around 257 kilometres south-east of Chicago, Indianapolis is another favourite stop in United States. Experience this destination's highlights firsthand at The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.