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Midway

$129+ 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 6/24. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — MDW
Jun 6 — Jun 131
Sat 6/6
Sat 6/13
1 adult, Economy
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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 May 7, 2026.

This Southwest deal was found by Cheapflights users on 5/5. 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 7/17:25 am
RIC
-
MDW
Nonstop1h 55m
Southwest
Tue 7/75:30 pm
MDW
-
RIC
1 stop3h 45m
Southwest
Deal found 5/5$310
This Southwest deal was found by Cheapflights users on 5/5. 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 9/153:30 pm
RIC
-
MDW
1 stop4h 35m
Southwest
Thu 9/176:15 pm
MDW
-
RIC
Nonstop2h 00m
Southwest
Deal found 5/5$311
This Southwest deal was found by Cheapflights users on 5/3. 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 6/107:25 am
RIC
-
MDW
Nonstop1h 55m
Southwest
Thu 6/1112:40 pm
MDW
-
RIC
Nonstop1h 50m
Southwest
Deal found 5/3$313
This Southwest deal was found by Cheapflights users on 5/2. 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.
Sat 6/136:30 am
RIC
-
MDW
2 stops7h 40m
Southwest
Wed 6/175:30 pm
MDW
-
RIC
1 stop3h 45m
Southwest
Deal found 5/2$315
This Delta deal was found by Cheapflights users on 5/4. 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 5/263:42 pm
RIC
-
MDW
1 stop6h 27m
Delta
Fri 5/2910:59 am
MDW
-
RIC
1 stop5h 21m
Delta
Deal found 5/4$320
This Southwest deal was found by Cheapflights users on 5/3. 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 5/286:00 am
RIC
-
MDW
2 stops8h 10m
Southwest
Tue 6/212:45 pm
MDW
-
RIC
2 stops8h 10m
Southwest
Deal found 5/3$321
This Southwest deal was found by Cheapflights users on 5/4. 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 6/104:55 pm
RIC
-
MDW
1 stop5h 40m
Southwest
Fri 6/1212:40 pm
MDW
-
RIC
Nonstop1h 50m
Southwest
Deal found 5/4$323
This Southwest deal was found by Cheapflights users on 5/3. 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 5/295:35 pm
RIC
-
MDW
1 stop5h 45m
Southwest
Tue 6/22:35 pm
MDW
-
RIC
2 stops6h 20m
Southwest
Deal found 5/3$325
This Southwest deal was found by Cheapflights users on 5/6. 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 6/21:40 pm
RIC
-
MDW
1 stop7h 20m
Southwest
Thu 6/42:40 pm
MDW
-
RIC
2 stops8h 10m
Southwest
Deal found 5/6$326
This Southwest deal was found by Cheapflights users on 5/6. 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 6/57:45 pm
RIC
-
MDW
Nonstop1h 55m
Southwest
Mon 6/88:05 pm
MDW
-
RIC
Nonstop1h 50m
Southwest
Deal found 5/6$327
This Southwest deal was found by Cheapflights users on 5/3. 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 5/297:30 pm
RIC
-
MDW
Nonstop2h 00m
Southwest
Mon 6/13:50 pm
MDW
-
RIC
2 stops6h 00m
Southwest
Deal found 5/3$329

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 May 7, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$310
(Southwest)

One-way from

$129
(Delta)

Popular in

May

Cheapest in

February

Average price

$487

Good round-trip deal

$414 or less

Good one-way deal

$193 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. 11% potential increase in price ($48 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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 May 7, 2026.
Use the filters below to find and compare flights from Richmond to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Wed 6/24

4:55 pm-11:35 pm

2 stops7h 40m

Chicago Midway

Wed 7/8

11:25 am-10:15 pm

2 stops9h 50m

$333

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Wed 7/8

4:55 pm-11:10 pm

2 stops7h 15m

Chicago Midway

Thu 7/9

8:05 pm-10:55 pm

Nonstop1h 50m

$338

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Wed 6/3

6:50 am-3:50 pm

2 stops10h 00m

Chicago Midway

Sat 6/6

5:00 am-1:00 pm

1 stop7h 00m

$341

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Mon 6/22

4:10 pm-9:25 pm

1 stop6h 15m

Chicago Midway

Wed 6/24

4:10 pm-10:15 pm

1 stop5h 05m

$343

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Sat 7/25

5:35 pm-10:25 pm

1 stop5h 50m

Chicago Midway

Wed 7/29

6:10 pm-9:05 pm

Nonstop1h 55m

$353

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Sat 7/11

6:35 pm-7:35 pm

Nonstop2h 00m

Chicago Midway

Mon 7/13

8:05 pm-10:55 pm

Nonstop1h 50m

$366

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Wed 10/14

7:25 am-8:20 am

Nonstop1h 55m

Chicago Midway

Sun 10/18

7:40 am-10:35 am

Nonstop1h 55m

$366

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Wed 7/1

12:20 pm-7:35 pm

2 stops8h 15m

Chicago Midway

Sat 7/11

8:00 am-5:55 pm

2 stops8h 55m

$373

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Sun 5/31

6:20 am-1:05 pm

2 stops7h 45m

Chicago Midway

Wed 6/3

12:45 pm-9:55 pm

2 stops8h 10m

$376
Quickest round-trip

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Thu 6/25

7:45 pm-8:40 pm

Nonstop1h 55m

Chicago Midway

Mon 6/29

8:05 pm-10:55 pm

Nonstop1h 50m

$389

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/6

Showing 1-10 of 23 resultsSorted by cheapest first
1
2
3

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 May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust 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 FlightHub the most. FlightHub 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, February is the cheapest month in which you can book a flight from Richmond to Chicago Midway Airport (average of $152). Flying from Richmond to Chicago Midway Airport in May is currently the most expensive (average of $487). 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 May 7, 2026.

It’s typically best to fly out from Richmond to Chicago Midway Airport at noon. Doing so could potentially save you 29% on the flight price compared to flying in the morning, which is usually more expensive.

How much does it cost to fly round-trip from Richmond to Chicago Midway Airport?

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 May 7, 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
7.9
Good
4,301 reviews

Crew

8.6

Boarding

8.1

Overall

7.9

Food

7.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
7.9
Good
4,301 reviews
Southwest
7.9
Good
4,301 reviews

Crew

8.6

Boarding

8.1

Overall

7.9

Food

7.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 are 0 flights 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 5h 40m. Southwest provides one of the quickest options available for as low as $315. The distance from Richmond to Chicago Midway Airport is about 628 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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 51% 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 $355 for a flight from Richmond to Chicago Midway Airport. The cheapest flight overall is $141 while the most popular route, (Richmond Byrd Intl - Chicago Midway) is currently priced at $251.

  • 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, February is the cheapest month in which you can book a flight from Richmond to Chicago Midway Airport (average of $152). Flying from Richmond to Chicago Midway Airport in May is currently the most expensive (average of $487). 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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

Browse thousands of different options on Cheapflights for your next trip

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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 May 7, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$178Average$369FlexibilityNo cancel feeOn-time63%

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