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Cheap flights from Richmond to Chicago from $119

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 11/4. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Richmond to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
8:10 am - 9:10 am-
2h 00mnonstop
Southwest Logo
3:45 pm - 8:25 pm-
3h 40m
$303Southwest
Sat, Aug 29 - Sat, Aug 29
Southwest Logo
3:40 pm - 8:35 pm-
5h 55m
Southwest Logo
6:15 pm - 9:20 pm-
2h 05mnonstop
$303Southwest
Sat, Sep 19 - Mon, Sep 21
Southwest Logo
4:25 pm - 9:00 pm-
5h 35m
Southwest Logo
11:55 am - 2:50 pm-
1h 55mnonstop
$303Southwest
Fri, Sep 4 - Tue, Sep 8
Southwest Logo
3:30 pm - 6:45 pm-
4h 15m
Southwest Logo
6:15 pm - 9:20 pm-
2h 05mnonstop
$303Southwest
Wed, Sep 16 - Thu, Sep 17
Southwest Logo
7:35 pm - 8:35 pm-
2h 00mnonstop
Southwest Logo
2:40 pm - 9:20 pm-
5h 40m
$303Southwest
Thu, Oct 8 - Sat, Oct 10
Southwest Logo
4:25 pm - 9:00 pm-
5h 35m
Southwest Logo
6:15 pm - 9:20 pm-
2h 05mnonstop
$303Southwest
Fri, Sep 25 - Mon, Sep 28
Southwest Logo
4:25 pm - 9:00 pm-
5h 35m
Southwest Logo
6:15 pm - 9:15 pm-
2h 00mnonstop
$303Southwest
Fri, Aug 28 - Mon, Aug 31
Southwest Logo
3:30 pm - 6:45 pm-
4h 15m
Southwest Logo
6:15 pm - 9:20 pm-
2h 05mnonstop
$303Southwest
Wed, Sep 2 - Fri, Sep 4
Delta Logo
5:36 am - 11:51 am-
7h 15m
Delta Logo
9:24 am - 4:36 pm-
6h 12m
$308Delta
Thu, Aug 27 - Sat, Aug 29
Delta Logo
5:36 am - 9:59 am-
5h 23m
Delta Logo
6:42 pm - 11:46 pm-
4h 04m
$308Delta
Thu, Aug 27 - Sat, Aug 29

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Southwest flights from Richmond to Chicago Midway Airport

Our best Southwest deals on Richmond to Chicago Midway Airport flight tickets
Southwest
Oct 9
RIC7:35 pmRichmond Byrd Intl
2h 00m
MDW8:35 pmChicago Midway
Oct 12
MDW5:00 amChicago Midway
4h 25m
1 stop
RIC10:25 amRichmond Byrd Intl
$303
Southwest
Sep 2
RIC6:15 amRichmond Byrd Intl
3h 45m
1 stop
MDW9:00 amChicago Midway
Sep 4
MDW8:10 amChicago Midway
10h 05m
2 stops
RIC7:15 pmRichmond Byrd Intl
$318
Southwest
Sep 5
RIC6:30 amRichmond Byrd Intl
11h 35m
2 stops
MDW5:05 pmChicago Midway
Sep 8
MDW11:10 amChicago Midway
8h 40m
2 stops
RIC8:50 pmRichmond Byrd Intl
$319

Delta flights from Richmond to Chicago Midway Airport

Our best Delta deals on Richmond to Chicago Midway Airport flight tickets
Delta
Aug 27
RIC5:36 amRichmond Byrd Intl
5h 23m
1 stop
MDW9:59 amChicago Midway
Aug 31
MDW6:05 amChicago Midway
4h 20m
1 stop
RIC11:25 amRichmond Byrd Intl
$308
Delta
Oct 2
RIC7:20 pmRichmond Byrd Intl
4h 24m
1 stop
MDW10:44 pmChicago Midway
Oct 5
MDW1:00 pmChicago Midway
4h 08m
1 stop
RIC6:08 pmRichmond Byrd Intl
$313
Delta
Aug 27
RIC5:36 amRichmond Byrd Intl
7h 15m
1 stop
MDW11:51 amChicago Midway
Aug 29
MDW6:11 amChicago Midway
5h 55m
1 stop
RIC1:06 pmRichmond Byrd Intl
$339

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 August 4, 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
Quickest round-trip

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Sat 8/29

8:10 am-9:10 am

Nonstop2h 00m

Chicago Midway

Sat 8/29

3:45 pm-8:25 pm

1 stop3h 40m

$303

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Sat 9/19

3:40 pm-8:35 pm

1 stop5h 55m

Chicago Midway

Mon 9/21

6:15 pm-9:20 pm

Nonstop2h 05m

$303

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Fri 9/4

4:25 pm-9:00 pm

1 stop5h 35m

Chicago Midway

Tue 9/8

11:55 am-2:50 pm

Nonstop1h 55m

$303

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Wed 9/16

3:30 pm-6:45 pm

1 stop4h 15m

Chicago Midway

Thu 9/17

6:15 pm-9:20 pm

Nonstop2h 05m

$303

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Thu 10/8

7:35 pm-8:35 pm

Nonstop2h 00m

Chicago Midway

Sat 10/10

2:40 pm-9:20 pm

1 stop5h 40m

$303

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Fri 9/25

4:25 pm-9:00 pm

1 stop5h 35m

Chicago Midway

Mon 9/28

6:15 pm-9:20 pm

Nonstop2h 05m

$303

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Fri 8/28

4:25 pm-9:00 pm

1 stop5h 35m

Chicago Midway

Mon 8/31

6:15 pm-9:15 pm

Nonstop2h 00m

$303

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Wed 9/2

3:30 pm-6:45 pm

1 stop4h 15m

Chicago Midway

Fri 9/4

6:15 pm-9:20 pm

Nonstop2h 05m

$303

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Thu 8/27

5:36 am-11:51 am

1 stop7h 15m

Chicago Midway

Sat 8/29

9:24 am-4:36 pm

1 stop6h 12m

$308

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Thu 8/27

5:36 am-9:59 am

1 stop5h 23m

Chicago Midway

Sat 8/29

6:42 pm-11:46 pm

1 stop4h 04m

$308

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 typical price of a round-trip flight between Richmond and Chicago Midway Airport?

Prices are currently typical for flights on this route.

Typical prices usually range from $295 to $417.
The lowest price recently found on this route was $303.

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, Wednesday is the cheapest day to fly to Chicago Midway Airport from Richmond. The lowest ticket price found for a Wednesday departure recently was $437. 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, Sunday 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 $498.

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 $315 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $487. 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 to Chicago Midway Airport flights?

There is only 1 cabin class available to choose from on Richmond to Chicago Midway Airport 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

$206

Fastest flight time

1h 55m

Direct flights

Mon, Tue, Thu, Fri, Sat and Sun
The best one-way flight to Chicago Midway Airport from Richmond in the past 72 hours is $206. The best round-trip flight deal from Richmond to Chicago Midway Airport found on momondo in the last 72 hours is $409.
The fastest flight from Richmond to Chicago Midway Airport takes 1h 55m
Direct flights go from Richmond to Chicago Midway Airport on Monday, Tuesday, Thursday, Friday, Saturday and Sunday. The only airline offering direct flights is Southwest.
Search flight deals

Frequently asked questions about flying from Richmond to Chicago Midway Airport

  • 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
4,222 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 2 flights on this route every week with an average price of $409. Southwest is rated 8.0/10 by our users.

Traveling to a place near Chicago?

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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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