Illinois

$100+ Cheap flights from Virginia to Illinois

RIC — ORD
Nov 29 — Dec 61
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Cheap flight deals from Virginia to Illinois

Cheapest flights from Virginia to Illinois

Fri 11/201:43 pm -
Nonstop2h 23m
Mon 11/306:27 pm -
Nonstop2h 05m
Deal found 10/28$234
Wed 12/308:32 am -
Nonstop2h 28m
Fri 1/15:21 am -
1 stop4h 04m
Deal found 10/28$265
Wed 11/256:03 pm -
1 stop5h 31m
Wed 12/25:23 am -
1 stop5h 27m
Deal found 10/28$271
Thu 12/171:13 pm -
Nonstop2h 19m
Sun 12/206:59 pm -
Nonstop2h 09m
Deal found 10/27$284
Thu 11/267:11 am -
Nonstop2h 09m
Thu 12/32:48 pm -
Nonstop2h 02m
Deal found 10/28$295
Thu 12/106:05 pm -
1 stop4h 25m
Fri 12/117:50 am -
2 stops8h 25m
Deal found 10/29$309
Fri 11/131:43 pm -
Nonstop2h 17m
Thu 11/196:27 pm -
Nonstop2h 05m
Deal found 10/29$309
Thu 12/38:00 am -
Nonstop2h 15m
Mon 12/78:00 am -
1 stop5h 25m
Deal found 10/29$311
Wed 11/256:07 pm -
1 stop6h 52m
Wed 12/25:23 am -
1 stop5h 56m
Deal found 10/28$311
Thu 11/1912:15 pm -
2 stops7h 10m
Mon 11/235:05 am -
1 stop4h 45m
Deal found 10/29$313
Fri 12/257:00 am -
Nonstop2h 39m
Tue 12/2910:30 am -
Nonstop2h 21m
Deal found 10/29$315
Sun 11/151:31 pm -
1 stop6h 14m
Sat 11/217:49 am -
1 stop10h 00m
Deal found 10/28$315

Find flight deals from Virginia to Illinois

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$234
(American Airlines)

One-way from

$100
(Priceline)

Popular in

November

Cheapest in

January

Average price

$378

Good round-trip deal

$333 or less

Good one-way deal

$165 or less
Provider with most accurate pricing for Norfolk-Chicago (CHI) flight deals.
Provider most trusted by Cheapflights users for Norfolk-Chicago (CHI) flights.
From Virginia to Illinois
One-way flight from Virginia to Illinois
Highest demand for flights based on searches. 6% potential increase in price ($25 potential increase over avg. RT price).
Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
Average for round-trip flights in October 2026
Price to beat on a round-trip flight from Virginia to Illinois.
Price to beat on a one-way flight from Virginia to Illinois.

Cheapflights Fare Finder

 
Use the filters below to find and compare flights from Virginia to Illinois that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

NorfolkChicago

ORF Norfolk - ORD Chicago O'Hare Intl

ORFORD

Norfolk

Mon 11/23

4:54 pm-12:43 am

1 stop8h 49m

Chicago O'Hare Intl

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$116

StauntonChicago

SHD Staunton Shenandoah Valley - ORD Chicago O'Hare Intl

SHDORD

Staunton Shenandoah Valley

Sat 11/21

1:43 pm-3:06 pm

Nonstop2h 23m

Chicago O'Hare Intl

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$119

RichmondChicago

RIC Richmond Byrd Intl - ORD Chicago O'Hare Intl

RICORD

Richmond Byrd Intl

Tue 11/17

8:00 am-9:33 am

Nonstop2h 33m

Chicago O'Hare Intl

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$130
Quickest round-trip

RichmondChicago

RIC Richmond Byrd Intl - MDW Chicago Midway

RICMDW

Richmond Byrd Intl

Tue 11/17

7:05 am-8:10 am

Nonstop2h 05m

Chicago Midway

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$130

NorfolkChicago

ORF Norfolk - MDW Chicago Midway

ORFMDW

Norfolk

Sat 12/5

3:10 pm-4:25 pm

Nonstop2h 15m

Chicago Midway

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$136

NorfolkChicago

ORF Norfolk - ORD Chicago O'Hare Intl

ORFORD

Norfolk

Tue 12/15

12:15 pm-1:59 pm

Nonstop2h 44m

Chicago O'Hare Intl

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$136

RichmondChicago

RIC Richmond Byrd Intl - ORD Chicago O'Hare Intl

RICORD

Richmond Byrd Intl

Tue 11/17

7:00 am-12:20 pm

1 stop6h 20m

Chicago O'Hare Intl

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$140

RichmondChicago

RIC Richmond Byrd Intl - ORD Chicago O'Hare Intl

RICORD

Richmond Byrd Intl

Tue 12/8

5:23 am-9:26 am

1 stop5h 03m

Chicago O'Hare Intl

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$140

NorfolkChicago

ORF Norfolk - ORD Chicago O'Hare Intl

ORFORD

Norfolk

Tue 11/3

1:44 pm-6:30 pm

1 stop5h 46m

Chicago O'Hare Intl

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$140

RichmondChicago

RIC Richmond Byrd Intl - MDW Chicago Midway

RICMDW

Richmond Byrd Intl

Tue 11/24

6:00 am-9:46 am

1 stop4h 46m

Chicago Midway

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$140

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 60 resultsSorted by cheapest first
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Best time to book a flight from Virginia to Illinois

Have a flexible travel schedule? Discover the best time to fly to Illinois from Virginia with our price prediction graph.
Estimated round-trip price

Cheapflights Insights

Everything you need to know about your flight from Virginia to Illinois

What is the cheapest month to book a flight from Virginia to Illinois?

Currently, January is the cheapest month in which you can book a flight from Virginia to Illinois (average of $351). Flying from Virginia to Illinois in July is currently the most expensive (average of $431). 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 VA to IL?

When flying from Virginia to Illinois, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 6% versus a flight in the morning.

How much does it cost to fly round-trip from Virginia to Illinois?

Airfare is below average for this route at the moment.
Virginia to Illinois flights typically cost between $329 and $485 in December.
The cheapest round-trip price found within the last 5 days was $315 on American Airlines (Dec 25-Dec 29).

How far ahead should I book a flight from Virginia to Illinois?

To ensure you get the cheapest price possible for a flight from Virginia to Illinois, you should look to book at least 28 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest day to fly from Virginia to Illinois?

Travelers seeking maximum savings on their Virginia to Illinois flight should consider departing on Friday at noon when fares are most often at their lowest. Sunday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Illinois

Get a feel of what it's like to fly with Southwest,Delta, andUnited Airlines from Virginia to Illinois by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.

Boarding

8.1

Overall

7.9

Food

7.0

Comfort

8.0

Entertainment

7.4

Crew

8.6

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Boarding

8.1

Overall

7.9

Food

7.0

Comfort

8.0

Entertainment

7.4

Crew

8.6

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Boarding

8.1

Overall

7.9

Food

7.0

Comfort

8.0

Entertainment

7.4

Crew

8.6

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Boarding

8.1

Overall

7.9

Food

7.0

Comfort

8.0

Entertainment

7.4

Crew

8.6

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Boarding

8.1

Overall

7.9

Food

7.0

Comfort

8.0

Entertainment

7.4

Crew

8.6

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Boarding

8.1

Overall

7.9

Food

7.0

Comfort

8.0

Entertainment

7.4

Crew

8.6

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Related info for your journey

  • How long is the flight from Virginia to Illinois?

    For as low as $234, American Airlines can have you in Illinois from Virginia in 2h 20m. The distance between Virginia and Illinois is about 540 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Virginia to Illinois one-way?

    $69 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on Southwest and United Airlines, with prices starting from $122 and $125, respectively.

  • Can I find deals for flights from Virginia to Illinois that include hotel bookings?

    Yes. In addition to deals on Virginia to Illinois flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Virginia to Illinois?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Virginia to Illinois.

  • Can I find deals for business class flights from Virginia to Illinois?

    Yes. Cheapflights offers flight deals from Virginia to Illinois 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 Virginia to Illinois?

    Currently, January is the cheapest month in which you can book a flight from Virginia to Illinois (average of $351). Flying from Virginia to Illinois in July is currently the most expensive (average of $431). 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

Browse thousands of different options on Cheapflights for your next trip

Alternative routes for Virginia to Illinois

Top 6 airlines flying from Virginia to Illinois

AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$169Average$402FlexibilityNo cancel feeOn-time69%
FrontierCheapest$176Average$397FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$220Average$352FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$233Average$360FlexibilityNo cancel feeOn-time71%
DeltaCheapest$236Average$349FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$290Average$418FlexibilityNo cancel feeOn-time63%

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