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Cheap flights from Richmond to Chicago from $69

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Richmond to Chicago departing on 12/23. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Cheap round-trip flights

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Multiple Airlines Logo
4:20 pm - 1:21 pmRIC-MDW
22h 01m1 stop
Multiple Airlines Logo
10:50 pm - 5:09 pmMDW-RIC
41h 19m2 stops
$264Multiple Airlines
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Tue, Dec 30 - Sun, Jan 4
Southwest Logo
5:30 pm - 6:35 pmRIC-MDW
2h 05mnonstop
Southwest Logo
6:40 am - 11:35 amMDW-RIC
3h 55m1 stop
$287Southwest
Find Deal
Wed, Dec 24 - Wed, Dec 31
Southwest Logo
5:30 pm - 6:35 pmRIC-MDW
2h 05mnonstop
Southwest Logo
1:50 pm - 4:40 pmMDW-RIC
1h 50mnonstop
$292Southwest
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Mon, Dec 15 - Tue, Dec 16
Southwest Logo
4:50 pm - 5:55 pmRIC-MDW
2h 05mnonstop
Southwest Logo
1:50 pm - 4:40 pmMDW-RIC
1h 50mnonstop
$293Southwest
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Thu, Dec 18 - Thu, Dec 25
Delta Logo
6:00 am - 8:54 amRIC-MDW
3h 54m1 stop
Delta Logo
9:34 am - 3:46 pmMDW-RIC
5h 12m1 stop
$297Delta
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Wed, Dec 10 - Wed, Dec 17
Multiple Airlines Logo
8:25 pm - 1:59 pmRIC-MDW
18h 34m2 stops
Multiple Airlines Logo
2:16 pm - 5:09 pmMDW-RIC
25h 53m1 stop
$298Multiple Airlines
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Sat, Dec 20 - Sun, Jan 4
Southwest Logo
5:30 pm - 6:35 pmRIC-MDW
2h 05mnonstop
Southwest Logo
1:50 pm - 4:40 pmMDW-RIC
1h 50mnonstop
$299Southwest
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Sat, Dec 6 - Tue, Dec 9
Southwest Logo
5:30 pm - 6:35 pmRIC-MDW
2h 05mnonstop
Southwest Logo
5:15 pm - 11:40 pmMDW-RIC
5h 25m1 stop
$302Southwest
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Wed, Dec 31 - Mon, Jan 5
Southwest Logo
5:30 pm - 6:35 pmRIC-MDW
2h 05mnonstop
Southwest Logo
5:35 pm - 8:25 pmMDW-RIC
1h 50mnonstop
$303Southwest
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Thu, Dec 11 - Sat, Dec 13
Southwest Logo
5:30 pm - 6:35 pmRIC-MDW
2h 05mnonstop
Southwest Logo
2:55 pm - 11:40 pmMDW-RIC
7h 45m2 stops
$307Southwest
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Wed, Dec 31 - Mon, Jan 5

Southwest flights from Richmond to Chicago Midway Airport

Our best Southwest deals on Richmond to Chicago Midway Airport flight tickets
Southwest
Nov 24
RIC6:00 pmRichmond Byrd Intl
6h 00m
1 stop
MDW11:00 pmChicago Midway
Nov 26
MDW7:55 amChicago Midway
8h 55m
2 stops
RIC5:50 pmRichmond Byrd Intl
$264
Find similar
Southwest
Nov 23
RIC12:00 pmRichmond Byrd Intl
9h 35m
2 stops
MDW8:35 pmChicago Midway
Nov 24
MDW2:55 pmChicago Midway
7h 45m
2 stops
RIC11:40 pmRichmond Byrd Intl
$269
Find similar
Southwest
Nov 24
RIC4:50 pmRichmond Byrd Intl
2h 05m
MDW5:55 pmChicago Midway
Nov 28
MDW9:35 amChicago Midway
1h 55m
RIC12:30 pmRichmond Byrd Intl
$274
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Delta flights from Richmond to Chicago Midway Airport

Our best Delta deals on Richmond to Chicago Midway Airport flight tickets
Delta
Dec 10
RIC6:00 amRichmond Byrd Intl
3h 54m
1 stop
MDW8:54 amChicago Midway
Dec 17
MDW9:34 amChicago Midway
5h 12m
1 stop
RIC3:46 pmRichmond Byrd Intl
$297
Find similar
Delta
Dec 6
RIC6:15 amRichmond Byrd Intl
4h 39m
1 stop
MDW9:54 amChicago Midway
Dec 9
MDW9:34 amChicago Midway
5h 12m
1 stop
RIC3:46 pmRichmond Byrd Intl
$319
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Delta
Dec 11
RIC12:36 pmRichmond Byrd Intl
6h 24m
1 stop
MDW6:00 pmChicago Midway
Dec 13
MDW4:29 pmChicago Midway
6h 49m
1 stop
RIC12:18 amRichmond Byrd Intl
$323
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momondo Fare Finder

 
Customize your flight search to find flights from Richmond to Chicago Midway Airport 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, momondo users made 832,500 searches. Data last updated November 21, 2025.
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

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Tue 12/30

4:20 pm-1:21 pm

1 stop22h 01m

Chicago Midway

Sun 1/4

10:50 pm-5:09 pm

2 stops41h 19m

$264

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Wed 12/24

5:30 pm-6:35 pm

Nonstop2h 05m

Chicago Midway

Wed 12/31

6:40 am-11:35 am

1 stop3h 55m

$287

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Mon 12/15

5:30 pm-6:35 pm

Nonstop2h 05m

Chicago Midway

Tue 12/16

1:50 pm-4:40 pm

Nonstop1h 50m

$292

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Thu 12/18

4:50 pm-5:55 pm

Nonstop2h 05m

Chicago Midway

Thu 12/25

1:50 pm-4:40 pm

Nonstop1h 50m

$293

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Wed 12/10

6:00 am-8:54 am

1 stop3h 54m

Chicago Midway

Wed 12/17

9:34 am-3:46 pm

1 stop5h 12m

$297

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Sat 12/20

8:25 pm-1:59 pm

2 stops18h 34m

Chicago Midway

Sun 1/4

2:16 pm-5:09 pm

1 stop25h 53m

$298

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Sat 12/6

5:30 pm-6:35 pm

Nonstop2h 05m

Chicago Midway

Tue 12/9

1:50 pm-4:40 pm

Nonstop1h 50m

$299

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Wed 12/31

5:30 pm-6:35 pm

Nonstop2h 05m

Chicago Midway

Mon 1/5

5:15 pm-11:40 pm

1 stop5h 25m

$302

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Thu 12/11

5:30 pm-6:35 pm

Nonstop2h 05m

Chicago Midway

Sat 12/13

5:35 pm-8:25 pm

Nonstop1h 50m

$303

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Wed 12/31

5:30 pm-6:35 pm

Nonstop2h 05m

Chicago Midway

Mon 1/5

2:55 pm-11:40 pm

2 stops7h 45m

$307

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Richmond to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago Midway Airport?

The month of August is, on average, the cheapest month to fly to Chicago Midway Airport from Richmond, with most prices found around $295. If you are unable to visit Chicago Midway Airport during the month of August, then departing from Richmond during the month October is also very affordable. Most momondo users find prices during this month for around $300.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Wednesday is the cheapest day to fly to Chicago Midway Airport from Richmond. The lowest ticket price found for a Wednesday departure recently was $409. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Monday is the most expensive day to depart from Richmond because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $517.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Richmond at noon is the least expensive time of day to depart. momondo users have found prices as low as $328 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $454. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Richmond Byrd Intl to Chicago Midway flight route?

Fly from Richmond Byrd Intl to Chicago Midway for the best Richmond Byrd Intl - Chicago Midway flight prices

What cabin class options are available on Richmond Byrd Intl to Chicago Midway flights?

There is only 1 cabin class available to choose from on Richmond Byrd Intl to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Richmond to Chicago Midway Airport flights?

No. A direct flight is the cheapest option for a flight between Richmond to Chicago Midway Airport.

When to book flights from Richmond to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Richmond to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Richmond to Chicago Midway Airport (RIC to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Richmond to Chicago Midway Airport

Best Price Found

$137

Fastest flight time

2h 00m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Richmond in the past 72 hours is $137. The best round-trip flight deal from Richmond to Chicago Midway Airport found on momondo in the last 72 hours is $386.
The fastest flight from Richmond to Chicago Midway Airport takes 2h 00m
Direct flights go from Richmond to Chicago Midway Airport every day.
Search flight deals

  • How far is Richmond Byrd Intl to Chicago Midway by plane?

    There are 620.7 mi between Richmond Byrd Intl and Chicago Midway. In terms of flight time, this usually takes a little over 2h 05m.

  • When did momondo last update prices for flights from Richmond Byrd Intl Airport to Chicago Midway Airport?

    Prices for flights from Richmond Byrd Intl Airport to Chicago Midway Airport were last updated today.

  • How many operators does momondo search for flights from Richmond Byrd Intl Airport to Chicago Midway Airport?

  • How old do you have to be to fly from Richmond Byrd Intl Airport to Chicago Midway Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Richmond Byrd Intl Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Richmond to Chicago Midway Airport?

  • What is the most popular airline from Richmond to Chicago Midway Airport?

Best airlines flying from Richmond to Chicago Midway Airport

Compare and see reviews for airlines that fly from Richmond to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $229Free CancellationRating
8.0
4,251 reviews
Search Southwest flights

  • Southwest Flights From Richmond to Chicago Midway Airport

    The lowest priced Southwest flight from Richmond to Chicago Midway Airport from the last 72 hours was $229. Generally, Southwest has 3 flights on this route every week with an average price of $371. Southwest is rated 8.0/10 by our users.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Richmond to Chicago?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Richmond to Chicago. momondo saves you time and could save you money on your trip.

Can I find flights from Richmond to Chicago with flexible booking policies on momondo?

momondo does allow users to show only those flights to Chicago from Richmond which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Richmond to Chicago?

Once all potential Richmond to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Richmond to Chicago right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Richmond and alert you when they change.

An easier way to manage your Chicago Midway Airport trip

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