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 5/25. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
Discover deals from 900+ travel sites with momondo.
Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.Price Alerts
Price Alerts
Not ready to book? to track prices.Find the cheapest flights from Virginia to Chicago
Cheap round-trip flights
Cheap one-way flights
Cheap last minute flights
Cheap direct flights
Spirit Airlines flights from Virginia to Chicago
Our best Spirit Airlines deals on Virginia to Chicago flight tickets
JetBlue flights from Virginia to Chicago
Our best JetBlue deals on Virginia to Chicago flight tickets
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 March is, on average, the cheapest month to fly to Chicago from Virginia, with most prices found around $338. If you’re not able to fly to Chicago in March, then September is your next best option. Flight prices from Virginia to Chicago during September average around $351.
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 $490. 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 $657.
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 in the afternoon. Flights from Virginia to Chicago during this time can be as low as $484. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $597.
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 16 weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $380 when searching 16 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 $283 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.
What is the cheapest airline that flies from Virginia to Chicago?
Frontier, Spirit Airlines, and American Airlines are the most popular carriers operating from Virginia to Chicago
What airlines fly to Chicago?
United Airlines, American Airlines and Southwest are the top three most popular airlines that fly to Chicago from Virginia according to our data. United Airlines is the first choice among our users, with 56% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 5 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.
How many flights depart from Virginia to Chicago on average per day?
As of April 2025, there are 134 flights per day flying from Virginia to Chicago. The most common time of day flights depart is 6:00AM, with 62% of flights taking off at noon.
How many flights depart from Virginia to Chicago on average per week?
The number of flights available between Virginia and Chicago is 940 per week as of April 2025. The most frequent departure day is Thu, with 17% of weekly flights leaving on this day.
Cheap Virginia to Chicago flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Virginia to Chicago
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?
There are 6 operators available for flights from Virginia to Chicago as of April 2025.
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?
Based on momondo bookings for flights between Virginia and Chicago, the leading plane model is Canadair (Bombardier) Regional Jet CRJ-550, making up 17.83% of the total bookings. Other popular models include Embraer ERJ-145 with 11.62%, Airbus A320-100/200 with 11.56%, and Boeing 737-700 Passenger/BBJ1 (winglets) with 9.00%.
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 | ||
|---|---|---|---|---|---|
| PriceFrom $105 | Free Cancellation | Rating 6.3 7,926 reviews | |||
| PriceFrom $148 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $176 | Free Cancellation | Rating 8.0 7,917 reviews | |||
| PriceFrom $187 | Free Cancellation | Rating 7.4 8,667 reviews | |||
| PriceFrom $268 | Free Cancellation | Rating 8.0 4,280 reviews |
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsWhy 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.