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Cheap flights from Virginia to Chicago from $45

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Virginia to Chicago departing on 2/4. 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
0 bags

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Find the cheapest flights from Virginia to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
7:19 pm - 6:24 pm
RDU
-
ORD
24h 05m1 stop
Multiple Airlines Logo
7:45 am - 10:48 am
ORD
-
RDU
2h 03mnonstop
$112Multiple Airlines
Thu, Jan 15 - Sun, Jan 18
Frontier Logo
10:20 am - 11:35 am
RDU
-
ORD
26h 15m1 stop
Frontier Logo
5:35 am - 8:40 am
ORD
-
RDU
2h 05mnonstop
$113Frontier
Fri, Jan 9 - Mon, Jan 12
Frontier Logo
6:10 am - 12:08 pm
RDU
-
ORD
6h 58m1 stop
Frontier Logo
7:45 am - 10:48 am
ORD
-
RDU
2h 03mnonstop
$114Frontier
Thu, Jan 15 - Sun, Jan 18
Multiple Airlines Logo
9:25 am - 10:53 am
RDU
-
ORD
2h 28mnonstop
Multiple Airlines Logo
7:21 pm - 9:53 am
ORD
-
RDU
13h 32m1 stop
$115Multiple Airlines
Mon, Jan 12 - Mon, Jan 12
Spirit Airlines Logo
3:08 pm - 9:13 pm
RDU
-
ORD
7h 05m1 stop
Spirit Airlines Logo
7:00 am - 2:13 pm
ORD
-
RDU
6h 13m1 stop
$124Spirit Airlines
Thu, Feb 26 - Mon, Mar 2
Southwest Logo
1:15 pm - 7:45 pm
RDU
-
MDW
7h 30m1 stop
Southwest Logo
1:25 pm - 4:15 pm
MDW
-
RDU
1h 50mnonstop
$173Southwest
Sat, Jan 17 - Sun, Jan 18
JetBlue Logo
11:55 am - 5:43 pm
DCA
-
ORD
6h 48m1 stop
JetBlue Logo
7:45 am - 2:34 pm
ORD
-
DCA
5h 49m1 stop
$176JetBlue
Wed, Feb 4 - Wed, Feb 11
JetBlue Logo
11:55 am - 5:43 pm
DCA
-
ORD
6h 48m1 stop
JetBlue Logo
7:45 am - 2:34 pm
ORD
-
DCA
5h 49m1 stop
$177JetBlue
Wed, Feb 4 - Wed, Feb 11
Southwest Logo
6:05 am - 7:20 am
DCA
-
MDW
2h 15mnonstop
Southwest Logo
8:35 pm - 11:20 pm
MDW
-
DCA
1h 45mnonstop
$204Southwest
Sat, Jan 17 - Sun, Jan 18
Spirit Airlines Logo
3:01 pm - 12:14 am
ORF
-
ORD
10h 13m1 stop
Spirit Airlines Logo
10:48 am - 9:50 pm
ORD
-
ORF
10h 02m1 stop
$255Spirit Airlines
Wed, Jan 7 - Sat, Jan 10

Spirit Airlines flights from Virginia to Chicago

Our best Spirit Airlines deals on Virginia to Chicago flight tickets
Spirit Airlines
Feb 26
RDU3:08 pmRaleigh-Durham
7h 05m
1 stop
ORD9:13 pmChicago O'Hare Intl
Mar 2
ORD7:00 amChicago O'Hare Intl
6h 13m
1 stop
RDU2:13 pmRaleigh-Durham
$124
Find similar
Spirit Airlines
Feb 27
RDU3:08 pmRaleigh-Durham
9h 39m
1 stop
ORD11:47 pmChicago O'Hare Intl
Mar 1
ORD7:00 amChicago O'Hare Intl
6h 13m
1 stop
RDU2:13 pmRaleigh-Durham
$134
Find similar
Spirit Airlines
Feb 27
RDU3:08 pmRaleigh-Durham
9h 39m
1 stop
ORD11:47 pmChicago O'Hare Intl
Mar 4
ORD5:15 amChicago O'Hare Intl
10h 56m
2 stops
RDU5:11 pmRaleigh-Durham
$140
Find similar

United Airlines flights from Virginia to Chicago

Our best United Airlines deals on Virginia to Chicago flight tickets
United Airlines
Jan 22
GSO5:25 pmGreensboro/H. Point
2h 24m
ORD6:49 pmChicago O'Hare Intl
Jan 27
ORD1:40 pmChicago O'Hare Intl
2h 04m
GSO4:44 pmGreensboro/H. Point
$204
Find similar
United Airlines
Jan 22
GSO8:00 amGreensboro/H. Point
2h 24m
ORD9:24 amChicago O'Hare Intl
Jan 27
ORD1:00 pmChicago O'Hare Intl
5h 01m
1 stop
GSO7:01 pmGreensboro/H. Point
$214
Find similar
United Airlines
Jan 17
DCA10:30 amWashington, D.C. Reagan-National
2h 16m
ORD11:46 amChicago O'Hare Intl
Jan 18
ORD7:00 amChicago O'Hare Intl
1h 58m
DCA9:58 amWashington, D.C. Reagan-National
$223
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Virginia to Chicago 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 December 23, 2025.
Use the filters below to find and compare flights from Virginia to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Thu 1/15

7:19 pm-6:24 pm

1 stop24h 05m

Chicago O'Hare Intl

Sun 1/18

7:45 am-10:48 am

Nonstop2h 03m

$112

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Fri 1/9

10:20 am-11:35 am

1 stop26h 15m

Chicago O'Hare Intl

Mon 1/12

5:35 am-8:40 am

Nonstop2h 05m

$113

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Thu 1/15

6:10 am-12:08 pm

1 stop6h 58m

Chicago O'Hare Intl

Sun 1/18

7:45 am-10:48 am

Nonstop2h 03m

$114

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Mon 1/12

9:25 am-10:53 am

Nonstop2h 28m

Chicago O'Hare Intl

Mon 1/12

7:21 pm-9:53 am

1 stop13h 32m

$115

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Thu 2/26

3:08 pm-9:13 pm

1 stop7h 05m

Chicago O'Hare Intl

Mon 3/2

7:00 am-2:13 pm

1 stop6h 13m

$124

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sat 1/17

1:15 pm-7:45 pm

1 stop7h 30m

Chicago Midway

Sun 1/18

1:25 pm-4:15 pm

Nonstop1h 50m

$173

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Wed 2/4

11:55 am-5:43 pm

1 stop6h 48m

Chicago O'Hare Intl

Wed 2/11

7:45 am-2:34 pm

1 stop5h 49m

$176

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Wed 2/4

11:55 am-5:43 pm

1 stop6h 48m

Chicago O'Hare Intl

Wed 2/11

7:45 am-2:34 pm

1 stop5h 49m

$177

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 1/17

6:05 am-7:20 am

Nonstop2h 15m

Chicago Midway

Sun 1/18

8:35 pm-11:20 pm

Nonstop1h 45m

$204

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Wed 1/7

3:01 pm-12:14 am

1 stop10h 13m

Chicago O'Hare Intl

Sat 1/10

10:48 am-9:50 pm

1 stop10h 02m

$255

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 Virginia to Chicago

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?

The month of September is, on average, the cheapest month to fly to Chicago from Virginia, with most prices found around $287. If you’re not able to fly to Chicago in September, then October is your next best option. Flight prices from Virginia to Chicago during October average around $310.

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

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $454. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Virginia to Chicago for around $583.

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

Our most recent data shows that the best time of day to fly to Chicago is at noon. Flights from Virginia to Chicago during this time can be as low as $457. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $505.

What is the cheapest Virginia to Chicago flight route?

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

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Virginia when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $357 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Virginia for as low as $223 on momondo.

What cabin class options are available on Virginia to Chicago flights?

There are 4 cabin classes available to choose from on Virginia to Chicago 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 Virginia to Chicago flights?

You could potentially save up to 31% on your flight if you consider stops on a Virginia to Chicago flight.

Cheap Virginia to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Virginia to Chicago

Best Price Found

$163

Fastest flight time

1h 53m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Virginia in the past 72 hours is $163. The best round-trip flight deal from Virginia to Chicago found on momondo in the last 72 hours is $233.
The fastest flight from Virginia to Chicago takes 1h 53m
Direct flights go from Virginia to Chicago every day.
There are 3 airports in Chicago. From Virginia there are direct flights to Chicago O'Hare Intl (ORD), Chicago Midway (MDW).
Search flight deals

  • When did momondo last update prices for flights from Virginia to Chicago?

    Prices for flights from Virginia to Chicago refresh daily.

  • How many operators does momondo search for flights from Virginia to Chicago?

  • How old do you have to be to fly from Virginia to Chicago?

    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 Virginia to Chicago.

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

    The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Virginia to Chicago?

Best airlines flying from Virginia to Chicago

Compare and see reviews for airlines that fly from Virginia to Chicago with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $65Free CancellationRating
6.3
8,194 reviews
Search Spirit Airlines flights
DeltaPriceFrom $108Free CancellationRating
7.9
8,014 reviews
Search Delta flights
FrontierPriceFrom $176Free CancellationRating
5.8
3,074 reviews
Search Frontier flights
SouthwestPriceFrom $181Free CancellationRating
8.0
4,253 reviews
Search Southwest flights
American AirlinesPriceFrom $209Free CancellationRating
7.2
11,050 reviews
Search American Airlines flights
United AirlinesPriceFrom $209Free CancellationRating
7.4
9,106 reviews
Search United Airlines flights

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 Virginia to Chicago?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Virginia to Chicago for you.

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

Yes. All flights to Chicago from Virginia on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

momondo helps you find the best flight between Virginia and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

Of course. momondo tracks the price of Virginia to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport