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$91+ 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 9/13. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — MDW
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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Cheap 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 August 14, 2025.

Round-trip from

$199
(Southwest)

One-way from

$91
(Kiwi.com)

Popular in

November

Cheapest in

August

Average price

$295

Good round-trip deal

$203 or less

Good one-way deal

$108 or less
From Richmond Byrd Intl to Chicago Midway
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One-way flight from Richmond Byrd Intl to Chicago Midway
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Highest demand for flights based on searches. 12% potential increase in price ($60 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Richmond Byrd Intl to Chicago Midway.
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Price to beat on a one-way flight from Richmond Byrd Intl to Chicago Midway.
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Find 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 August 14, 2025.

This Southwest deal was found by Cheapflights users on 8/12. 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 9/247:30 amRIC - MDW
Nonstop1h 55mSouthwest
Wed 10/85:35 amMDW - RIC
1 stop4h 20mSouthwest
Deal found 8/12$199
This Southwest deal was found by Cheapflights users on 8/14. 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.
Mon 9/154:25 pmRIC - MDW
Nonstop2h 00mSouthwest
Tue 9/1611:00 amMDW - RIC
Nonstop1h 55mSouthwest
Deal found 8/14$203
This Delta deal was found by Cheapflights users on 8/13. 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.
Wed 9/106:00 amRIC - MDW
1 stop3h 35mDelta
Wed 9/176:15 pmMDW - RIC
1 stop4h 06mDelta
Deal found 8/13$209
This Southwest deal was found by Cheapflights users on 8/13. 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.
Mon 11/175:30 pmRIC - MDW
Nonstop2h 05mSouthwest
Thu 11/201:50 pmMDW - RIC
Nonstop1h 50mSouthwest
Deal found 8/13$217
This Southwest deal was found by Cheapflights users on 8/14. 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.
Sun 9/147:00 pmRIC - MDW
Nonstop2h 00mSouthwest
Tue 9/1611:00 amMDW - RIC
Nonstop1h 55mSouthwest
Deal found 8/14$218
This Delta deal was found by Cheapflights users on 8/14. 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.
Thu 10/166:00 amRIC - MDW
1 stop3h 40mDelta
Tue 10/216:00 amMDW - RIC
1 stop4h 21mDelta
Deal found 8/14$223
This Southwest deal was found by Cheapflights users on 8/14. 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 9/255:20 pmRIC - MDW
1 stop5h 15mSouthwest
Mon 9/2910:55 amMDW - RIC
Nonstop1h 55mSouthwest
Deal found 8/14$227
This Southwest deal was found by Cheapflights users on 8/13. 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.
Sun 9/147:00 pmRIC - MDW
Nonstop2h 00mSouthwest
Thu 9/1810:55 amMDW - RIC
Nonstop1h 55mSouthwest
Deal found 8/13$232

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 August 14, 2025.
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 9/24

7:30 am-8:25 am

Nonstop1h 55m

Chicago Midway

Wed 10/8

5:35 am-10:55 am

1 stop4h 20m

$199

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Mon 9/15

4:25 pm-5:25 pm

Nonstop2h 00m

Chicago Midway

Tue 9/16

11:00 am-1:55 pm

Nonstop1h 55m

$203

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Mon 9/29

4:25 pm-5:25 pm

Nonstop2h 00m

Chicago Midway

Wed 10/1

11:00 am-1:55 pm

Nonstop1h 55m

$203

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Thu 10/2

3:50 pm-4:50 pm

Nonstop2h 00m

Chicago Midway

Tue 10/7

1:25 pm-4:15 pm

Nonstop1h 50m

$203

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Wed 9/10

6:00 am-8:35 am

1 stop3h 35m

Chicago Midway

Wed 9/17

6:15 pm-11:21 pm

1 stop4h 06m

$209

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Mon 11/17

5:30 pm-6:35 pm

Nonstop2h 05m

Chicago Midway

Thu 11/20

1:50 pm-4:40 pm

Nonstop1h 50m

$217

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Sat 9/13

7:00 am-9:18 am

1 stop27h 18m

$91

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Tue 9/16

7:30 am-8:25 am

Nonstop1h 55m

$95

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Wed 12/17

5:30 pm-6:35 pm

Nonstop2h 05m

$95

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Tue 10/21

8:20 am-9:20 am

Nonstop2h 00m

$95

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/12

Showing 1-10 of 13 results
1
2

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, April is the cheapest month in which you can book a flight from Richmond to Chicago Midway Airport (average of $160). Flying from Richmond to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 August 14, 2025.

It’s typically best to fly out from Richmond to Chicago Midway Airport in the afternoon. Doing so could potentially save you 27% on the flight price compared to flying in the evening, 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 August 14, 2025.
See what other customers who have flown with Southwest and Delta 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
4,244 reviews

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,244 reviews
Southwest
8.0
Very good
4,244 reviews

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Delta
8.0
Very good
7,980 reviews
Southwest
8.0
Very good
4,244 reviews

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

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 2 different airlines.

  • What are the cheapest airlines flying from Richmond to Chicago Midway Airport round-trip?

    Cheapflights users have booked flights from Richmond to Chicago Midway Airport round-trip from $270. Another airline that can offer you cheap pricing is Delta. Southwest is currently priced 34% 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 $241 for a flight from Richmond to Chicago Midway Airport. The cheapest flight overall is $53 while the most popular route, (Richmond Byrd Intl - Chicago Midway) is currently priced at $203.

  • 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, April is the cheapest month in which you can book a flight from Richmond to Chicago Midway Airport (average of $160). Flying from Richmond to Chicago Midway Airport in November is currently the most expensive (average of $249). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Alternative routes for Richmond to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Richmond to Midway

Discover the top 2 airlines 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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$270Average$369FlexibilityNo cancel feeOn-time63%
DeltaCheapest$320Average$487FlexibilityNo cancel feeOn-timeN/A

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