RIC - MDW

$87 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 9/25. 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

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
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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

Wed, Sep 24 - Wed, Oct 8
Southwest Logo
7:30 am - 8:25 amRIC-MDW
1h 55mnonstop
Southwest Logo
5:35 am - 10:55 amMDW-RIC
4h 20m1 stop
$199Southwest
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Thu, Oct 2 - Sun, Oct 5
 Logo
7:00 am - 8:53 amRIC-MDW
26h 53m1 stop
 Logo
10:13 am - 12:13 pmMDW-RIC
25h 00m1 stop
Mon, Sep 15 - Tue, Sep 16
Southwest Logo
4:25 pm - 5:25 pmRIC-MDW
2h 00mnonstop
Southwest Logo
11:00 am - 1:55 pmMDW-RIC
1h 55mnonstop
$203Southwest
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Wed, Sep 10 - Wed, Sep 17
Delta Logo
6:00 am - 8:35 amRIC-MDW
3h 35m1 stop
Delta Logo
6:15 pm - 11:21 pmMDW-RIC
4h 06m1 stop
$209Delta
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Mon, Sep 15 - Tue, Sep 16
Southwest Logo
6:10 am - 9:00 amRIC-MDW
3h 50m1 stop
Southwest Logo
11:00 am - 1:55 pmMDW-RIC
1h 55mnonstop
$213Southwest
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Wed, Sep 24 - Wed, Oct 8
Southwest Logo
6:20 am - 12:10 pmRIC-MDW
6h 50m2 stops
Southwest Logo
5:35 am - 10:55 amMDW-RIC
4h 20m1 stop
$214Southwest
Find Deal
Mon, Nov 17 - Thu, Nov 20
Southwest Logo
5:30 pm - 6:35 pmRIC-MDW
2h 05mnonstop
Southwest Logo
1:50 pm - 4:40 pmMDW-RIC
1h 50mnonstop
$217Southwest
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Thu, Oct 2 - Sun, Oct 5
 Logo
6:33 pm - 8:53 amRIC-MDW
15h 20m2 stops
 Logo
10:13 am - 12:13 pmMDW-RIC
25h 00m1 stop
Thu, Oct 16 - Tue, Oct 21
Delta Logo
6:00 am - 8:40 amRIC-MDW
3h 40m1 stop
Delta Logo
6:00 am - 11:21 amMDW-RIC
4h 21m1 stop
$223Delta
Find Deal
Thu, Oct 16 - Tue, Oct 21
Delta Logo
6:00 am - 8:40 amRIC-MDW
3h 40m1 stop
Delta Logo
10:35 am - 4:33 pmMDW-RIC
4h 58m1 stop
$291Delta
Find Deal
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 Wednesday and more expensive on a Monday. On your return trip to Richmond, you should consider flying back on a Sunday, and avoid Mondays 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 August, where tickets cost $295 (return) on average. On the other hand, the most expensive months are November and September, where the average cost of round-trip tickets is $590 and $580 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 $225, prices are generally cheapest when you fly direct.

Good to know

Low seasonFebruary
Cheapest flight$87
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly and prices are also 8% 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 $87 for a one-way ticket and $199 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, Delta, JetBlue, 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.

  • 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 $369 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 $487 and an overall rating of 8.0.

  • 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 $108 or less one-way and $203 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 airlines 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 4244 reviews
8.1Boarding
7.5Entertainment
8.6Crew
7.0Food
8.0Comfort
Airline reviews

Southwest's seats are the least comfortable I have ever sat in.

4.0 OkayDavid, Aug 2025DTW - STL
Read more Southwest reviews

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Other than a bit of a delay, everything was good. Again, the boarding process and picking seats is the only thing I don't enjoy.

If we are going to have to pay for luggage, make it easier to do. Put something on the app during check-in so I don't need to do it at the kiosk. I've done it twice recently and I ended up having to pay at the desk because something went wrong at the kiosk in Tampa.

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

Very smooth checking in our luggage with a super pleasant SW agent. I enjoyed a fun entertaining movie.

WiFi did not work. For as outrageous as these flights cost, when they’re advertised with certain services/ features they should be in working order

On this flight I felt the food offering was not as complete as on previous flights. The tomato salad was a bit off and there was nothing additional such a bread or butter. The breakfast was only one option, so you either ate what they had or ate nothing. The crew was efficient, but most seemed frustrated throughout the flight. The flight arrived early and was obstacle-free, so I’m overall quite happy, but the shine in the rest of the experience just wasn’t there.

The seats got pretty uncomfortable pretty fast. The armrests are bigger than on other planes, so I had less room in the actual seat. My butt hurt by the end of the flight. :/ comfort was the primary issue. The crew were fantastic!

I believe that a four-hour trip should have a meal. Delta had none.

Great flight with Delta! Boarding was quick and easy, the amenities were solid, and the plane was in great shape. The flight attendants had a fun, lively energy while staying professional. All in all, a smooth trip — even managed to catch up on some rest. Thanks, Delta!

I was uncomfortably cold on the plane. Other than that it was uneventful and therefore as enjoyable as a plane ride can be.

There was supposed to be a meal served, but there wasn’t and the major toilet was out of order

They made us board and then deboard due to mechanical issue which delayed the departure by almost 2 hours and we barely made our connecting flight. These quality checks should've been done before boarding not after.

Having to up charge for a seat assignment is not good. Delta can do better

I liked the friendliness of the staff. The cleanliness of all 3 planes.

Was charged for my luggage despite having been on one ticket from an international flight. Too tired to argue after 15 hours on flight. Was charged for rechecking it at JFK airport. Not sure why those off Kenya Airways were required to do that.

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

Information on your arrival and departure airports

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