- Must visit
Art Institute Of Chicago
One of the premier art museums in the US, known for Impressionist masterpieces, modern works, and the iconic bronze lions at its entrance.
Flights from Virginia Beach, VA to Chicago, IL depart on average 40 times per day, taking around 2h 22m. Cheap flight tickets for this journey start at $442 (€362) but you can travel from only $209 (€171) by train.
There are 3 flights per day. The earliest flight runs at 05:00, the last at 21:40. The fastest flight covers the 712 miles (1146 km) distance in 2h 35m. May is the cheapest month to fly.
Distance 712 miles (1146 km) |
Average flight duration 2h 22m |
Cheapest ticket price $442 (€362) |
Flights per day 40 |
Direct flights 3 |
Fastest flight 2h 35m |
First flight 5:00 AM |
Last flight 9:40 PM |
Cheapest Month May |
Cheapest Day Mon |
High Season Jan - Mar |
Low Season Jul - Sep |
Omio recommends booking the train as it is the most popular option from Virginia Beach, VA to Chicago, IL among Omio's users. If you are prioritising price take the train with prices starting from $209. For those with little time consider booking a flight which can get you there in 2h 22m. The ticket price range depends on the travel mode: a train costs an average of $209, and a flight costs an average of $442.
Distance: 712 miles (1146 km)
| Flight | Most popular Train | Bus | Driving |
|---|---|---|---|
$442 Average price | $209 Average price Cheapest | $291 Average price | $174 Average price (fuel + tolls) |
5h 22m Average total duration Fastest 2h 22m Onboard + 3h 0m Additional time* | 23h 30m Average total duration 23h 0m Onboard + 30m Additional time* | 32h 4m Average total duration 31h 34m Onboard + 30m Additional time* | 13h 35m Average total duration (door-to-door) |
Direct Options | Direct Options | Direct Options | Direct Options |
This is compared to other travel options from Virginia Beach, VA to Chicago, IL:
A train is $82 (€68) less than a bus for this route with tickets for a bus from Virginia Beach, VA to Chicago, IL costing on average $291 (€239).
A train is $233 (€191) less than a flight for this route with tickets for a flight from Virginia Beach, VA to Chicago, IL costing on average $442 (€362).
Other travel options to Chicago, IL take longer:
Train takes on average 23h 0m.
Bus takes on average 31h 34m.
Compare bus, train, and flight prices over the next three weeks. See the best deals at a glance, find the lowest fares, and choose the option that fits your budget.
Discover the best of Chicago — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Chicago trip today.
One of the premier art museums in the US, known for Impressionist masterpieces, modern works, and the iconic bronze lions at its entrance.
Major natural history museum famous for Sue the T. rex, ancient cultures, and extensive science collections that appeal to both adults and children.
Large hands-on science museum in Hyde Park featuring a submarine, space exhibits, engineering displays, and immersive family-friendly experiences.
The city’s signature public space, home to Cloud Gate, gardens, events, and major skyline views that define modern Chicago.
Famous stretch of Michigan Avenue lined with historic buildings, shops, hotels, and frequent first-time visitor photo stops.
Highly popular waterfront promenade with architecture views, bridges, and one of the best urban walks in the city.
Chicago’s iconic thick-crust pizza baked in a deep pan, layered with cheese, toppings, and chunky tomato sauce. It is one of the city’s most famous comfort foods.
An all-beef hot dog on a poppy seed bun topped with mustard, onions, neon relish, tomato, pickle spear, sport peppers, and celery salt. It is a classic local street food.
Thinly sliced roast beef piled onto an Italian roll, often dipped in seasoned jus and topped with sweet peppers or giardiniera. It is a defining Chicago sandwich.
A historic old-school steakhouse serving steaks, chops, and classic Italian-American dishes in a traditional setting.
Chicago’s internationally acclaimed fine-dining restaurant known for highly inventive tasting menus and exceptional service.
A long-established Chicago favorite known for buttery deep-dish pizza and a casual, family-friendly atmosphere.
Moderate for a major U.S. city: casual food is manageable, but hotels, attractions, and downtown dining can be pricey.
Tip 18-20% in restaurants; 20%+ for great service. Tip bartenders USD 1-2 per drink, taxis about 10-15%, and hotel staff a few dollars.
Find answers to the most common questions about traveling from Virginia Beach, VA to Chicago, IL by flight. From journey times and ticket prices to direct connections, first and last departures, and even whether the route is scenic, our FAQs cover everything you need to plan your trip. Whether you’re looking for the fastest flight, the cheapest option, or tips for making the most of your visit at Chicago, IL, this guide helps you travel smarter and with confidence.

Here are some other resources that might have the information you need