Journey information
Overview: Portsmouth, VA to Chicago, IL flight
Flights from Portsmouth, VA to Chicago, IL depart on average 17 times per day, taking around 2h 34m. Cheap flight tickets for this journey start at $438 (€350) but you can travel from only $317 (€253) by bus.
There are 2 flights per day. The earliest flight runs at 21:45, the last at 21:45. The fastest flight covers the 697 miles (1123 km) distance in 2h 34m. April is the cheapest month to fly.
Distance 697 miles (1123 km) |
Average flight duration 2h 34m |
Cheapest ticket price $438 (€350) |
Flights per day 17 |
Direct flights 2 |
Fastest flight 2h 34m |
First flight 9:45 PM |
Last flight 9:45 PM |
Cheapest Month Apr |
Cheapest Day Thu |
High Season Jan - Mar |
Low Season Apr - Jun |
Travel Information
Compare train, bus, and flight for Portsmouth, VA to Chicago, IL
Omio recommends booking the train as it is the most popular option from Portsmouth, VA to Chicago, IL among Omio's users. If you are prioritising price take the bus with prices starting from $317. For those with little time consider booking a flight which can get you there in 2h 34m. The ticket price range depends on the travel mode: a bus costs an average of $317, and a train costs an average of $463.
Distance: 697 miles (1123 km)
Compare flight with
| Flight | Most popular Train | Bus |
|---|---|---|
$438 Average price | $463 Average price | $317 Average price Cheapest |
5h 34m Average total duration Fastest 2h 34m Onboard + 3h 0m Additional time* | 25h 3m Average total duration 24h 33m Onboard + 30m Additional time* | 38h 35m Average total duration 38h 5m Onboard + 30m Additional time* |
Direct Options | Direct Options | Direct Options |
This is compared to other travel options from Portsmouth, VA to Chicago, IL:
A bus is $120 (€96) less than a flight for this route with tickets for a flight from Portsmouth, VA to Chicago, IL costing on average $438 (€350).
A bus is $146 (€117) less than a train for this route with tickets for a train from Portsmouth, VA to Chicago, IL costing on average $463 (€370).
Other travel options to Chicago, IL take longer:
Train takes on average 24h 33m.
Bus takes on average 38h 5m.
Compare prices and tickets Portsmouth, VA to Chicago, IL by train, bus, or flight
Compare train, bus, 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.
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FAQs: Portsmouth, VA to Chicago, IL Flight
Find answers to the most common questions about traveling from Portsmouth, 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.

- Millennium Park, a public park known for its modern art installations and the iconic Cloud Gate sculpture
- Art Institute of Chicago, a renowned museum housing an extensive collection of art from around the world
- Navy Pier, a popular entertainment destination featuring rides, restaurants, and lakefront views
- Willis Tower Skydeck, an observation deck offering panoramic views of the city from one of the tallest buildings in the Western Hemisphere
- Field Museum, a natural history museum with vast exhibits including the famous T. rex skeleton, Sue.
- Chicago Air and Water Show, an exhilarating display of military and civilian aircraft performing daring maneuvers over Lake Michigan
- Lollapalooza, a massive music festival featuring top artists across multiple genres in Grant Park
- Chicago Gourmet, a premier culinary event celebrating the city's vibrant food scene with tastings, cooking demonstrations, and wine pairings.
- Memorial Day, the unofficial start of summer with vibrant outdoor activities and events
- Independence Day, spectacular fireworks and festive celebrations throughout the city
- Labor Day, a lively atmosphere with various festivals and pleasant weather.
- Museum of Science and Industry, an interactive museum featuring exhibits on science, technology, and industry
- Explore the vibrant neighborhoods of Chicago, such as Wicker Park and Lincoln Park, known for their unique shops and eateries
- Take a river cruise to see the city's iconic architecture from a different perspective
- Attend a live performance at the historic Chicago Theatre
- Enjoy a day at Lincoln Park Zoo, one of the oldest zoos in the U.S., offering free admission.
popular airports
Popular airports from Portsmouth, VA to Chicago, IL
- Free Wi-Fi available throughout the airport.
- Shops are located in all terminals, including duty-free and brands like Hudson and MAC Cosmetics.
- Parking available with options including hourly, daily, and economy lots, approximately 2.85€ ($3) per hour.
- Restaurants are located in all terminals, offering a variety of cuisines including American and intertiol. Top options include Tortas Frontera and Publican Tavern.
- Available outside the terminal.
- Elevators, ramps, toilets
- Available throughout the airport.
- Hotels such as Hilton Chicago O'Hare are located on airport grounds, with others like the Hyatt Regency nearby.
- Showers are available in some lounges, such as the United Club, but access may require a fee or membership.
- Lounges available, including United Club and American Airlines Admirals Club.
- Lost and Found located in terminal 1, near the baggage claim area.
- Car rental services are available at the Multi-Modal Facility, with companies like Hertz and Avis.
- CTA Blue Line, O'Hare Station, 45 minutes to city center
More options for your journey from Portsmouth, VA to Chicago, IL
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