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$99+ Cheap flights from Virginia to Illinois

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 7/22. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — ORD
Jun 28 — Jul 51
Sun 6/28
Sun 7/5
1 adult, Economy
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Cheap flight deals from Virginia to Illinois

Cheapest flights from Virginia to Illinois
Explore the most affordable flight options available from Virginia to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 29, 2026.

This Kiwi.com deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/78:29 pm
RDU
-
ORD
1 stop27h 41m
Multiple Airlines
Wed 8/125:13 pm
ORD
-
RDU
1 stop23h 37m
Multiple Airlines
Deal found 5/28$232
This American Airlines deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/33:25 pm
DCA
-
ORD
Nonstop2h 24m
American Airlines
Thu 11/58:00 am
ORD
-
DCA
Nonstop1h 59m
American Airlines
Deal found 5/25$233
This Kiwi.com deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/288:29 pm
RDU
-
ORD
1 stop27h 45m
Multiple Airlines
Tue 9/15:30 pm
ORD
-
RDU
1 stop14h 49m
Multiple Airlines
Deal found 5/25$233
This Southwest deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/186:00 am
DCA
-
MDW
2 stops7h 05m
Southwest
Thu 8/202:50 pm
MDW
-
DCA
1 stop6h 05m
Southwest
Deal found 5/26$233
This American Airlines deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/2410:10 pm
DCA
-
ORD
Nonstop2h 20m
American Airlines
Sat 6/276:00 am
ORD
-
DCA
Nonstop2h 14m
American Airlines
Deal found 5/28$236
This Southwest deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/66:50 pm
DCA
-
MDW
1 stop4h 05m
Southwest
Tue 8/118:50 am
MDW
-
DCA
2 stops6h 00m
Southwest
Deal found 5/26$236
This United Airlines deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/247:15 am
DCA
-
ORD
Nonstop2h 14m
United Airlines
Sat 6/276:00 am
ORD
-
DCA
Nonstop1h 54m
United Airlines
Deal found 5/28$237
This United Airlines deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/136:10 am
IAD
-
ORD
Nonstop2h 17m
United Airlines
Wed 7/151:30 pm
ORD
-
IAD
Nonstop2h 00m
United Airlines
Deal found 5/28$237
This United Airlines deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/18:05 am
RDU
-
ORD
Nonstop2h 26m
United Airlines
Sat 7/46:55 am
ORD
-
RDU
Nonstop2h 13m
United Airlines
Deal found 5/24$237
This Southwest deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/206:10 am
DCA
-
MDW
Nonstop2h 00m
Southwest
Wed 7/15:20 pm
MDW
-
DCA
1 stop4h 55m
Southwest
Deal found 5/28$237
This Delta deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/168:00 am
DCA
-
ORD
1 stop5h 40m
Delta
Mon 9/215:10 pm
ORD
-
DCA
1 stop4h 54m
Delta
Deal found 5/25$238
This Delta deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/195:25 pm
IAD
-
ORD
1 stop4h 02m
Delta
Sat 8/221:50 pm
ORD
-
IAD
1 stop5h 15m
Delta
Deal found 5/24$238

Find flight deals from Virginia to Illinois

Keep the following information in mind while searching for Virginia to Illinois flight deals. Data was last updated May 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$232
(Kiwi.com)

One-way from

$99
(American Airlines)

Popular in

March

Cheapest in

September

Average price

$373

Good round-trip deal

$233 or less

Good one-way deal

$133 or less
Provider with most accurate pricing for Norfolk-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Norfolk-Chicago (CHI) flights.
Search Deals
From Virginia to Illinois
Search Deals
One-way flight from Virginia to Illinois
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($24 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals
Price to beat on a round-trip flight from Virginia to Illinois.
Search Deals
Price to beat on a one-way flight from Virginia to Illinois.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Virginia to Illinois 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, Cheapflights users made 2,558,603 searches. Data last updated May 29, 2026.
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

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Thu 8/20

1:00 pm-5:50 pm

1 stop5h 50m

Chicago Midway

Wed 8/26

8:50 am-3:50 pm

2 stops6h 00m

$233

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Mon 7/6

6:30 am-7:46 am

Nonstop2h 16m

Chicago O'Hare Intl

Wed 7/8

9:00 am-11:59 am

Nonstop1h 59m

$247

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 11/5

6:10 am-8:45 am

1 stop3h 35m

Chicago Midway

Tue 11/10

6:45 pm-11:02 pm

1 stop3h 17m

$248

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Thu 7/9

12:23 pm-6:29 pm

1 stop7h 06m

Chicago O'Hare Intl

Wed 7/15

2:07 pm-6:59 pm

1 stop3h 52m

$257

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Tue 6/23

7:45 pm-11:26 pm

1 stop4h 41m

Chicago O'Hare Intl

Tue 6/30

2:13 pm-5:27 pm

Nonstop2h 14m

$257

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Tue 6/30

6:00 am-10:50 am

1 stop5h 50m

Chicago O'Hare Intl

Mon 7/27

5:18 pm-10:59 pm

1 stop4h 41m

$257

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Tue 6/16

9:39 am-12:46 pm

1 stop4h 07m

Chicago Midway

Wed 6/17

1:26 pm-6:59 pm

1 stop4h 33m

$258

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Fri 9/18

1:15 pm-2:05 pm

Nonstop1h 50m

Chicago Midway

Tue 9/22

12:45 pm-6:50 pm

2 stops5h 05m

$265

Washington, D.C.St. Louis

IAD - STL

IADSTL

Washington, D.C. Dulles Intl

Tue 7/7

10:31 am-3:46 pm

1 stop6h 15m

Lambert-St Louis

Tue 7/14

8:43 am-11:55 am

Nonstop2h 12m

$267

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Fri 7/3

7:59 pm-11:59 pm

1 stop5h 00m

Chicago O'Hare Intl

Tue 7/7

9:45 am-4:20 pm

1 stop5h 35m

$267

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/27

Showing 1-10 of 60 resultsSorted by cheapest first
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6

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
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

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, August is the cheapest month in which you can book a flight from Virginia to Illinois (average of $70). Flying from Virginia to Illinois in November is currently the most expensive (average of $849). 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?

Find hourly flight availability from Virginia to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 29, 2026.

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 afternoon, which can drop the price by up to 5% versus a flight in the morning.

Weekly flight availability from Virginia to Illinois

Explore weekly flight availability from Virginia to Illinois. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated May 29, 2026.

The most flights from USVA to USIL are scheduled on a Thursday (29 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (16 on average).

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

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 88 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?

Use this chart to determine the cheapest time to fly round-trip from Virginia to Illinois. Price data was last updated on May 23, 2026.

Travelers seeking maximum savings on their Virginia to Illinois flight should consider departing on Wednesday 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 insights into the airlines that provide service to Illinois. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Illinois. Reviews last updated May 29, 2026.
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.
Southwest
8.0
Very good
4,264 reviews

Food

7.0

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,264 reviews
Southwest
8.0
Very good
4,264 reviews

Food

7.0

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Delta
7.9
Good
8,419 reviews
Southwest
8.0
Very good
4,264 reviews

Food

7.0

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,763 reviews
Southwest
8.0
Very good
4,264 reviews

Food

7.0

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,643 reviews
Southwest
8.0
Very good
4,264 reviews

Food

7.0

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Frontier
5.6
Fair
2,929 reviews
Southwest
8.0
Very good
4,264 reviews

Food

7.0

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Related info for your journey

Find useful and relevant information for your journey from Virginia to Illinois. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Virginia to Illinois?

    For as low as $247, Southwest can have you in Illinois from Virginia in 2h 16m. The distance between Virginia and Illinois is about 610 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?

    $53 is the cheapest one-way deal found within the past few days, from Southwest. You may also be able to find cheap deals on Frontier and American Airlines, with prices starting from $69 and $90, 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, August is the cheapest month in which you can book a flight from Virginia to Illinois (average of $70). Flying from Virginia to Illinois in November is currently the most expensive (average of $849). 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

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Alternative routes for Virginia to Illinois

See prices for flight routes from nearby airports that may be better suited for you.
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Top 7 airlines flying from Virginia to Illinois

Discover the top 7 airlines that operate flights from Virginia to Illinois. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$72Average$354FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$92Average$291FlexibilityNo cancel feeOn-time65%
DeltaCheapest$98Average$266FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$126Average$352FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$169Average$387FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$178Average$375FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$203Average$356FlexibilityNo cancel feeOn-time71%

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