Cheap flights from Chicago to Virginia from $92
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Virginia departing on 12/3. 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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Fly from
Fly to
Route
Depart
Return
ChicagoStaunton
ORD Chicago O'Hare Intl - SHD Staunton Shenandoah Valley
ORDSHD
Chicago O'Hare Intl
Wed 11/4
6:20 pm-9:19 pm
Nonstop1h 59m
Staunton Shenandoah Valley
Sat 11/7
1:43 pm-3:00 pm
Nonstop2h 17m
ChicagoStaunton
ORD Chicago O'Hare Intl - SHD Staunton Shenandoah Valley
ORDSHD
Chicago O'Hare Intl
Mon 11/2
6:20 pm-9:19 pm
Nonstop1h 59m
Staunton Shenandoah Valley
Mon 11/9
1:43 pm-3:00 pm
Nonstop2h 17m
ChicagoRichmond
ORD Chicago O'Hare Intl - RIC Richmond Byrd Intl
ORDRIC
Chicago O'Hare Intl
Tue 11/10
1:30 pm-8:28 pm
1 stop5h 58m
Richmond Byrd Intl
Sat 11/14
7:28 am-12:20 pm
1 stop5h 52m
ChicagoRichmond
ORD Chicago O'Hare Intl - RIC Richmond Byrd Intl
ORDRIC
Chicago O'Hare Intl
Wed 11/11
7:05 am-12:18 pm
1 stop4h 13m
Richmond Byrd Intl
Sat 11/14
4:56 pm-9:42 pm
1 stop5h 46m
ChicagoRichmond
MDW Chicago Midway - RIC Richmond Byrd Intl
MDWRIC
Chicago Midway
Sat 11/14
10:05 am-7:00 pm
2 stops7h 55m
Richmond Byrd Intl
Tue 11/17
4:40 pm-9:30 pm
1 stop5h 50m
ChicagoRichmond
MDW Chicago Midway - RIC Richmond Byrd Intl
MDWRIC
Chicago Midway
Tue 11/3
6:00 am-11:40 am
1 stop4h 40m
Richmond Byrd Intl
Tue 11/3
4:40 pm-10:40 pm
2 stops7h 00m
ChicagoNorfolk
ORD Chicago O'Hare Intl - ORF Norfolk
ORDORF
Chicago O'Hare Intl
Thu 11/26
2:52 pm-6:59 pm
2 stops27h 07m
Norfolk
Mon 11/30
7:34 pm-7:15 am
1 stop12h 41m
ChicagoNorfolk
MDW Chicago Midway - ORF Norfolk
MDWORF
Chicago Midway
Wed 10/28
6:42 pm-12:46 pm
1 stop17h 04m
Norfolk
Tue 11/3
1:44 pm-11:47 pm
1 stop11h 03m
ChicagoRichmond
ORD Chicago O'Hare Intl - RIC Richmond Byrd Intl
ORDRIC
Chicago O'Hare Intl
Thu 10/22
5:58 pm-9:10 pm
Nonstop2h 12m
Richmond Byrd Intl
Mon 10/26
8:20 pm-12:02 am
1 stop4h 42m
ChicagoNorfolk
ORD Chicago O'Hare Intl - ORF Norfolk
ORDORF
Chicago O'Hare Intl
Sat 10/31
7:29 am-10:53 am
Nonstop2h 24m
Norfolk
Sat 11/7
3:46 pm-5:30 pm
Nonstop2h 44m
See travel insights to Virginia from
How to get the cheapest flight ticket from Chicago to Virginia
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 Virginia?
The month of January is, on average, the cheapest month to fly to Virginia from Chicago, with most prices found around $350. If you don’t want to visit Virginia in January, then you should wait until December to fly from Chicago, when ticket prices are also cheap, with an average price of $381.
What is the cheapest day to depart on your flight to Virginia?
On average, the least expensive day to fly to Virginia from Chicago is on a Saturday. momondo users have found tickets for Saturday departures for as low as $368. However, this price may fluctuate depending on the airline, the season, and holidays. Be sure to avoid booking your departure on a Monday as prices are generally higher than usual. According to our data, the average ticket price to Virginia on Monday is $461.
What is the cheapest time of day to depart on your flight to Virginia?
Our data shows that the cheapest Chicago to Virginia flights are usually those with departure times in the morning. Our users have found flights to Virginia in the morning for as low as $392. In the evening is when there is more demand to fly to Virginia, so prices are often more expensive at around $410 per ticket.
What is the cheapest Chicago to Virginia flight route?
Fly from Chicago O'Hare Intl to Staunton Shenandoah Valley for the best Chicago - Virginia flight prices
How far in advance should I book a flight from Chicago to Virginia?
You are more likely to see cheaper flights to Virginia from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Virginia for around $382 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Virginia from Chicago for as low as $269 on momondo.
What cabin class options are available on Chicago to Virginia flights?
There are 4 cabin classes available to choose from on Chicago to Virginia flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
What is the cheapest airline that flies from Chicago to Virginia?
Southwest, Delta, and Frontier are the most popular carriers operating from Chicago to Virginia
What airlines fly to Virginia?
United Airlines, American Airlines and Southwest are the top three most popular airlines that fly to Virginia from Chicago according to our data. United Airlines is the first choice among our users, with 57% of people opting to fly with this airline when traveling to Virginia. Keep in mind that there are 4 different airlines that fly to Virginia on a routine basis, so you have a few additional options to choose from.
How many flights depart from Chicago to Virginia on average per day?
As of October 2026, there are 53 flights per day flying from Chicago to Virginia. The most common time of day flights depart is 5:00PM, with 45% of flights taking off in the afternoon.
How many flights depart from Chicago to Virginia on average per week?
374 flights are operational weekly from Chicago to Virginia as of October 2026. The most popular departure day for this route is Sun, with 18% of flights per week taking off on this day.
Cheap Chicago to Virginia flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago to Virginia
Frequently asked questions about flying from Chicago to Virginia
When did momondo last update prices for flights from Chicago to Virginia?
Prices for flights from Chicago to Virginia were last updated today.
How many operators does momondo search for flights from Chicago to Virginia?
The number of operators available for flights from Chicago to Virginia is 4 as of October 2026.
How old do you have to be to fly from Chicago to Virginia?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Virginia.
What documentation or ID do you need to fly to Virginia?
The travel and health documents required for your trip to Virginia 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 Virginia. 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 Chicago to Virginia?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Chicago to Virginia is Embraer 175 (Enhanced Winglets) (21.98% of total bookings). The next most popular plane models are Embraer 175 (18.51%), Canadair (Bombardier) Regional Jet CRJ-550 (14.79%), and Canadair (Bombardier) Regional Jet 700 (10.11%).
Best airlines flying from Chicago to Virginia
Compare and see reviews for airlines that fly from Chicago to Virginia with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $165 | Free Cancellation | Rating 7.9 4,212 reviews | |||
| PriceFrom $209 | Free Cancellation | Rating 7.0 12,127 reviews | |||
| PriceFrom $226 | Free Cancellation | Rating 5.5 2,550 reviews | |||
| PriceFrom $226 | Free Cancellation | Rating 7.4 10,285 reviews |
Why use momondo?
Why should I use momondo to find a flight deal from Chicago to Virginia?
Finding the right flight to Virginia from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Virginia quick and easy, saving you time and money.
Can I find flights from Chicago to Virginia with flexible booking policies on momondo?
Flights from Chicago to Virginia with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.
How can momondo help me find flights from Chicago to Virginia?
Once all potential Chicago to Virginia 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 Chicago to Virginia right now. Can momondo alert me if prices change?
If you are not ready to book a flight from Chicago to Virginia now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Virginia and let you know when they change.