HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$74+ Cheap flights from Richmond (RIC) to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/12. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — MDW
Feb 20 — Feb 271
Fri 2/20
Fri 2/27
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Richmond to Midway with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Richmond to Midway

Cheapest flights from Richmond to Midway
Explore the most affordable flight options available from Richmond to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 21, 2026.

This Southwest deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/107:10 am
RIC
-
MDW
2 stops8h 20m
Southwest
Tue 2/179:50 am
MDW
-
RIC
Nonstop1h 55m
Southwest
Deal found 1/20$300
This Southwest deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/107:30 pm
RIC
-
MDW
Nonstop2h 00m
Southwest
Wed 4/156:00 pm
MDW
-
RIC
Nonstop1h 55m
Southwest
Deal found 1/20$302
This Kiwi.com deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/18:17 am
RIC
-
MDW
2 stops12h 35m
Multiple Airlines
Mon 2/26:20 am
MDW
-
RIC
1 stop11h 09m
Multiple Airlines
Deal found 1/20$304
This Southwest deal was found by Cheapflights users on 1/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/228:05 am
RIC
-
MDW
Nonstop2h 05m
Southwest
Sat 4/252:15 pm
MDW
-
RIC
1 stop4h 40m
Southwest
Deal found 1/21$305
This Southwest deal was found by Cheapflights users on 1/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/197:25 pm
RIC
-
MDW
Nonstop2h 05m
Southwest
Tue 3/246:10 pm
MDW
-
RIC
Nonstop1h 50m
Southwest
Deal found 1/21$312
This Kiwi.com deal was found by Cheapflights users on 1/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/196:29 pm
RIC
-
MDW
1 stop19h 39m
Multiple Airlines
Mon 3/239:51 pm
MDW
-
RIC
1 stop18h 40m
Multiple Airlines
Deal found 1/21$314
This KAYAK deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/106:05 am
RIC
-
MDW
2 stops26h 15m
Southwest
Fri 2/139:40 am
MDW
-
RIC
Nonstop1h 55m
Southwest
Deal found 1/20$315
This Kiwi.com deal was found by Cheapflights users on 1/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/68:11 am
RIC
-
MDW
2 stops12h 56m
Multiple Airlines
Thu 4/99:20 am
MDW
-
RIC
1 stop7h 11m
Multiple Airlines
Deal found 1/21$316
This Delta deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/35:40 am
RIC
-
MDW
1 stop5h 14m
Delta
Tue 3/36:20 pm
MDW
-
RIC
1 stop3h 59m
Delta
Deal found 1/20$317
This Southwest deal was found by Cheapflights users on 1/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/97:30 pm
RIC
-
MDW
Nonstop2h 00m
Southwest
Mon 4/1312:55 pm
MDW
-
RIC
Nonstop1h 55m
Southwest
Deal found 1/21$319
This Southwest deal was found by Cheapflights users on 1/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/114:05 pm
RIC
-
MDW
2 stops7h 00m
Southwest
Thu 2/129:40 am
MDW
-
RIC
Nonstop1h 55m
Southwest
Deal found 1/21$320

Find flight deals from Richmond to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Richmond (RIC) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$300
(Southwest)

One-way from

$74
(Kiwi.com)

Popular in

January

Cheapest in

August

Average price

$839

Good round-trip deal

$392 or less

Good one-way deal

$253 or less
Provider with most accurate pricing for Richmond Byrd Intl-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Richmond Byrd Intl-Chicago Midway flights.
Search Deals
From Richmond Byrd Intl to Chicago Midway
Search Deals
One-way flight from Richmond Byrd Intl to Chicago Midway
Search Deals
Highest demand for flights based on searches. 25% potential increase in price ($137 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 10% potential price decrease ($40 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals
Price to beat on a round-trip flight from Richmond Byrd Intl to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Richmond Byrd Intl to Chicago Midway.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Richmond to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 21, 2026.
Use the filters below to find and compare flights from Richmond to Chicago Midway Airport that are best for you.

Fly from

Richmond

Fly to

Midway

Route

Depart

Return

Price

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Wed 5/13

8:05 am-9:10 am

Nonstop2h 05m

Chicago Midway

Wed 5/20

12:45 pm-9:50 pm

2 stops8h 05m

$300

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Tue 2/10

4:05 pm-7:00 pm

1 stop3h 55m

Chicago Midway

Tue 2/17

11:50 am-10:40 pm

2 stops9h 50m

$310

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Fri 3/13

7:25 pm-8:30 pm

Nonstop2h 05m

Chicago Midway

Wed 3/18

6:10 pm-9:00 pm

Nonstop1h 50m

$312

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Wed 2/11

6:05 am-9:05 am

1 stop4h 00m

Chicago Midway

Thu 2/12

9:40 am-12:35 pm

Nonstop1h 55m

$315

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Fri 4/10

7:30 pm-8:30 pm

Nonstop2h 00m

Chicago Midway

Wed 4/15

12:45 pm-9:50 pm

2 stops8h 05m

$317

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Thu 4/9

7:30 pm-8:30 pm

Nonstop2h 00m

Chicago Midway

Mon 4/13

12:55 pm-3:50 pm

Nonstop1h 55m

$319

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Fri 4/10

6:00 am-8:53 am

1 stop3h 53m

Chicago Midway

Tue 4/14

10:49 am-6:49 pm

1 stop7h 00m

$322

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Wed 3/4

5:40 am-9:54 am

1 stop5h 14m

Chicago Midway

Mon 3/9

10:45 am-6:19 pm

1 stop6h 34m

$322

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Fri 3/13

7:25 pm-8:30 pm

Nonstop2h 05m

Chicago Midway

Sat 3/14

6:30 am-11:00 am

1 stop3h 30m

$322

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Mon 3/2

1:08 pm-7:07 pm

2 stops30h 59m

$125

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

Showing 1-10 of 20 results
1
2

Compare providers for flights from Richmond to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Richmond to Midway in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
PricelinePrice Accuracy1 starTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Richmond-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Richmond-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Richmond-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Richmond-Chicago Midway Airport flights, Cheapflights users trust Expedia the most. Expedia has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Richmond-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Richmond to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Richmond with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Richmond to Chicago Midway Airport

What is the cheapest month to book a flight from Richmond to Chicago Midway Airport?

Currently, March is the cheapest month in which you can book a flight from Richmond to Chicago Midway Airport (average of $53). Flying from Richmond to Chicago Midway Airport in January is currently the most expensive (average of $141). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from RIC to MDW?

Find hourly flight availability from Richmond to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 21, 2026.

It’s typically best to fly out from Richmond to Chicago Midway Airport at noon. Doing so could potentially save you 26% on the flight price compared to flying in the morning, which is usually more expensive.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated January 21, 2026.
See what other customers who have flown with Southwest from Richmond to Chicago Midway Airport have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,266 reviews

Boarding

8.1

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,266 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.1

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Related info for your journey

Find useful and relevant information for your journey from Richmond to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Richmond to Chicago Midway?

    If you book a flight to Chicago Midway from Richmond, you will be flying from Byrd Intl, which is the city’s only airport. Richmond Byrd Intl (RIC) is located 6.9 mi from the center of Richmond. There is 1 flight from Byrd Intl to Chicago Midway per day from 1 airline.

  • How long is the flight from Richmond to Chicago Midway Airport?

    A quick flight from Richmond to Chicago Midway Airport can take about 2h 05m. Southwest provides one of the quickest options available for as low as $300. The distance from Richmond to Chicago Midway Airport is about 628 mi. Most flights are nonstop.

  • What is the cheapest airline to fly from Richmond to Chicago Midway Airport round-trip?

    Cheapflights users have booked flights from Richmond to Chicago Midway Airport round-trip from $178. Southwest is currently priced 56% below the average price you’ll pay for this route.

  • What are the cheapest flights from Richmond to Chicago Midway Airport?

    On average you can expect to pay $393 for a flight from Richmond to Chicago Midway Airport. The cheapest flight overall is $132 while the most popular route, (Richmond Byrd Intl - Chicago Midway) is currently priced at $229.

  • Can I find deals for flights from Richmond to Midway that include hotel bookings?

    Yes. In addition to deals on Richmond to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Richmond to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Richmond to Midway.

  • Can I find deals for business class flights from Richmond to Midway?

    Yes. Cheapflights offers flight deals from Richmond to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

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

    Currently, March is the cheapest month in which you can book a flight from Richmond to Chicago Midway Airport (average of $53). Flying from Richmond to Chicago Midway Airport in January is currently the most expensive (average of $141). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Richmond to Midway

See prices for flight routes from nearby airports that may be better suited for you.
Dulles Intl to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Dulles Intl to Midway flights
Raleigh to O'Hare Intl flights
Reagan-National to Midway flights
Richmond to O'Hare Intl flights
Raleigh to Midway flights
Norfolk to O'Hare Intl flights
Greensboro to O'Hare Intl flights
Charlottesville to O'Hare Intl flights
Norfolk to Midway flights
Roanoke to O'Hare Intl flights
Greensboro to Midway flights
Charlottesville to Midway flights
Blountville to O'Hare Intl flights
Roanoke to Midway flights
Lynchburg to O'Hare Intl flights
Norfolk to Rockford flights
Blountville to Midway flights
Staunton to O'Hare Intl flights
Newport News to O'Hare Intl flights
Raleigh to Rockford flights
Richmond to Rockford flights
Lewisburg to O'Hare Intl flights
Salisbury to O'Hare Intl flights
Newport News to Midway flights

Top airline flying from Richmond to Midway

Discover the top airline that operate flights from Richmond to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$178Average$349FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.