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Cheap flights from Richmond to Chicago from $96

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 4/23. 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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0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
5:35 pm - 10:20 pm
RIC
-
MDW
5h 45m
1 stop
Southwest Logo
2:10 pm - 10:50 pm
MDW
-
RIC
7h 40m
2 stops
$290Southwest
Thu, Apr 23 - Mon, Apr 27
Southwest Logo
6:05 am - 12:15 pm
RIC
-
MDW
7h 10m
2 stops
Southwest Logo
12:45 pm - 10:50 pm
MDW
-
RIC
9h 05m
2 stops
$295Southwest
Sat, May 2 - Sat, May 9
Southwest Logo
5:35 pm - 6:35 am
RIC
-
MDW
14h 00m
2 stops
Southwest Logo
7:40 am - 9:55 pm
MDW
-
RIC
13h 15m
2 stops
$296Southwest
Mon, Apr 13 - Wed, Apr 15
Southwest Logo
6:05 am - 2:40 pm
RIC
-
MDW
9h 35m
2 stops
Southwest Logo
8:00 am - 12:55 pm
MDW
-
RIC
3h 55m
1 stop
$300Southwest
Sat, Apr 18 - Wed, Apr 22
Multiple Airlines Logo
12:20 pm - 10:19 pm
RIC
-
MDW
10h 59m
1 stop
Multiple Airlines Logo
6:00 am - 7:50 pm
MDW
-
RIC
12h 50m
2 stops
$301Multiple Airlines
Thu, Apr 16 - Mon, Apr 20
Multiple Airlines Logo
12:20 pm - 7:31 pm
RIC
-
MDW
8h 11m
1 stop
Multiple Airlines Logo
2:15 pm - 7:50 pm
MDW
-
RIC
28h 35m
2 stops
$302Multiple Airlines
Thu, Apr 16 - Thu, Apr 23
Multiple Airlines Logo
12:20 pm - 10:19 pm
RIC
-
MDW
10h 59m
1 stop
Multiple Airlines Logo
2:15 pm - 7:50 pm
MDW
-
RIC
28h 35m
2 stops
$305Multiple Airlines
Thu, Apr 16 - Thu, Apr 23
Southwest Logo
7:30 pm - 8:30 pm
RIC
-
MDW
2h 00mnonstop
Southwest Logo
6:00 pm - 8:55 pm
MDW
-
RIC
1h 55mnonstop
$313Southwest
Fri, May 1 - Tue, May 5
Southwest Logo
7:30 pm - 8:30 pm
RIC
-
MDW
2h 00mnonstop
Southwest Logo
12:45 pm - 9:55 pm
MDW
-
RIC
8h 10m
2 stops
$315Southwest
Mon, May 18 - Wed, May 20
Southwest Logo
6:50 am - 2:05 pm
RIC
-
MDW
8h 15m
2 stops
Southwest Logo
2:10 pm - 10:50 pm
MDW
-
RIC
7h 40m
2 stops
$317Southwest
Tue, Apr 28 - Thu, Apr 30

Southwest flights from Richmond to Chicago Midway Airport

Our best Southwest deals on Richmond to Chicago Midway Airport flight tickets
Southwest
Apr 23
RIC5:35 pmRichmond Byrd Intl
5h 45m
1 stop
MDW10:20 pmChicago Midway
Apr 27
MDW2:10 pmChicago Midway
7h 40m
2 stops
RIC10:50 pmRichmond Byrd Intl
$290
Southwest
May 2
RIC6:05 amRichmond Byrd Intl
7h 10m
2 stops
MDW12:15 pmChicago Midway
May 9
MDW12:45 pmChicago Midway
9h 05m
2 stops
RIC10:50 pmRichmond Byrd Intl
$295
Southwest
Apr 13
RIC5:35 pmRichmond Byrd Intl
14h 00m
2 stops
MDW6:35 amChicago Midway
Apr 15
MDW7:40 amChicago Midway
13h 15m
2 stops
RIC9:55 pmRichmond Byrd Intl
$296

Delta flights from Richmond to Chicago Midway Airport

Our best Delta deals on Richmond to Chicago Midway Airport flight tickets
Delta
Jun 4
RIC6:00 amRichmond Byrd Intl
3h 43m
1 stop
MDW8:43 amChicago Midway
Jun 9
MDW6:00 amChicago Midway
6h 48m
1 stop
RIC1:48 pmRichmond Byrd Intl
$328
Delta
May 26
RIC3:42 pmRichmond Byrd Intl
6h 27m
1 stop
MDW9:09 pmChicago Midway
May 29
MDW6:23 amChicago Midway
7h 12m
1 stop
RIC2:35 pmRichmond Byrd Intl
$333
Delta
Apr 10
RIC6:08 pmRichmond Byrd Intl
5h 23m
1 stop
MDW10:31 pmChicago Midway
Apr 14
MDW10:41 amChicago Midway
5h 33m
1 stop
RIC5:14 pmRichmond Byrd Intl
$343

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 March 21, 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

Thu 4/23

5:35 pm-10:20 pm

1 stop5h 45m

Chicago Midway

Mon 4/27

2:10 pm-10:50 pm

2 stops7h 40m

$290

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Sat 5/2

6:05 am-12:15 pm

2 stops7h 10m

Chicago Midway

Sat 5/9

12:45 pm-10:50 pm

2 stops9h 05m

$295

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Mon 4/13

5:35 pm-6:35 am

2 stops14h 00m

Chicago Midway

Wed 4/15

7:40 am-9:55 pm

2 stops13h 15m

$296

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Sat 4/18

6:05 am-2:40 pm

2 stops9h 35m

Chicago Midway

Wed 4/22

8:00 am-12:55 pm

1 stop3h 55m

$300

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Thu 4/16

12:20 pm-10:19 pm

1 stop10h 59m

Chicago Midway

Mon 4/20

6:00 am-7:50 pm

2 stops12h 50m

$301

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Thu 4/16

12:20 pm-7:31 pm

1 stop8h 11m

Chicago Midway

Thu 4/23

2:15 pm-7:50 pm

2 stops28h 35m

$302

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Thu 4/16

12:20 pm-10:19 pm

1 stop10h 59m

Chicago Midway

Thu 4/23

2:15 pm-7:50 pm

2 stops28h 35m

$305
Quickest round-trip

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Fri 5/1

7:30 pm-8:30 pm

Nonstop2h 00m

Chicago Midway

Tue 5/5

6:00 pm-8:55 pm

Nonstop1h 55m

$313

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Mon 5/18

7:30 pm-8:30 pm

Nonstop2h 00m

Chicago Midway

Wed 5/20

12:45 pm-9:55 pm

2 stops8h 10m

$315

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Tue 4/28

6:50 am-2:05 pm

2 stops8h 15m

Chicago Midway

Thu 4/30

2:10 pm-10:50 pm

2 stops7h 40m

$317

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 February is, on average, the cheapest month to fly to Chicago Midway Airport from Richmond, with most prices found around $152. If you are unable to visit Chicago Midway Airport during the month of February, then departing from Richmond during the month January is also very affordable. Most momondo users find prices during this month for around $286.

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

According to our data, Friday is the cheapest day to fly to Chicago Midway Airport from Richmond. The lowest ticket price found for a Friday departure recently was $397. 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 $466.

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 $336 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $455. 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?

You could potentially save up to 25% on your flight if you consider stops on a Richmond to Chicago Midway Airport flight.

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

$183

Fastest flight time

1h 55m

Direct flights

Mon, Wed, Thu, Fri, Sat and Sun
The best one-way flight to Chicago Midway Airport from Richmond in the past 72 hours is $183. The best round-trip flight deal from Richmond to Chicago Midway Airport found on momondo in the last 72 hours is $379.
The fastest flight from Richmond to Chicago Midway Airport takes 1h 55m
Direct flights go from Richmond to Chicago Midway Airport on Monday, Wednesday, Thursday, Friday, Saturday and Sunday. There are no airlines offering direct flights.
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 1h 55m.

  • 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 $178Free CancellationRating
8.0
4,325 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 $178. Generally, Southwest has 4 flights on this route every week with an average price of $349. 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
Valparaiso
Schererville
Munster
Crown Point
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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