- Must visit
Glenstone
A Major contemporary art museum and landscape destination in Montgomery County. It is farther from Silver Spring but among the region's most sought-after art experiences.
Flights from Chicago, IL to Silver Spring, MD depart on average 73 times per day, taking around 14h 16m. Cheap flight tickets for this journey start at $427 (€349) but you can travel from only $134 (€110) by bus.
There are 21 flights per day. The earliest flight runs at 05:00, the last at 22:45. The fastest flight covers the 592 miles (953 km) distance in 14h 16m. October is the cheapest month to fly.
Distance 592 miles (953 km) |
Average flight duration 14h 16m |
Cheapest ticket price $427 (€349) |
Flights per day 73 |
Direct flights 21 |
Fastest flight 14h 16m |
First flight 5:00 AM |
Last flight 10:45 PM |
Cheapest Month Oct |
Cheapest Day Thu |
High Season Oct - Dec |
Low Season Jan - Mar |
Omio recommends booking the bus as it is the most popular option from Chicago, IL to Silver Spring, MD among Omio's users. If you are prioritising price take the bus with prices starting from $134. For those with little time consider booking a flight which can get you there in 14h 16m. The ticket price range depends on the travel mode: a bus costs an average of $134, and a flight costs an average of $427.
Distance: 592 miles (953 km)
| Flight | Most popular Bus | Train | Driving |
|---|---|---|---|
$427 Average price | $134 Average price Cheapest | $238 Average price | $138 Average price (fuel + tolls) |
17h 16m Average total duration Fastest 14h 16m Onboard + 3h 0m Additional time* | 19h 28m Average total duration 18h 58m Onboard + 30m Additional time* | 24h 19m Average total duration 23h 49m Onboard + 30m Additional time* | 10h 16m Average total duration (door-to-door) |
Direct Options | Direct Options | Direct Options | Direct Options |
This is compared to other travel options from Chicago, IL to Silver Spring, MD:
A bus is $104 (€85) less than a train for this route with tickets for a train from Chicago, IL to Silver Spring, MD costing on average $238 (€195).
A bus is $292 (€239) less than a flight for this route with tickets for a flight from Chicago, IL to Silver Spring, MD costing on average $427 (€349).
Other travel options to Silver Spring, MD take longer:
Bus takes on average 18h 58m.
Train takes on average 23h 49m.
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 Silver Spring — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Silver Spring trip today.
A Major contemporary art museum and landscape destination in Montgomery County. It is farther from Silver Spring but among the region's most sought-after art experiences.
A Federal museum with medical history collections, pathology specimens, and exhibits on military medicine and public health. A distinctive local museum near downtown Silver Spring.
A Historic cinema and film culture venue known for preservation and special screenings. Not a museum, but an important cultural institution and Art Deco landmark in Silver Spring.
The city's main urban core with plazas, shops, entertainment venues, and frequent public events. It is the essential area for first-time visitors.
A Central public square used for festivals, ice skating in season, concerts, and community events.
A Beautiful public garden with seasonal displays, conservatories, and photogenic landscapes. Very popular for leisurely visits and social media photos.
Pan-seared cakes of sweet blue crab with minimal filler, a Chesapeake staple widely loved in the Silver Spring area.
A smoky, spicy sausage associated with the Washington area, usually served on a bun with chili, onions, and mustard.
Fried chicken wings or carryout dishes served with sweet-tangy Mumbo sauce, a beloved Washington regional flavor.
Polished seafood and chophouse spot highlighting Mid-Atlantic oysters, crab, steaks, and classic cocktails.
Classic Jewish deli and Silver Spring institution known for pastrami, matzo ball soup, and old-school charm.
Long-running Burmese restaurant known for tea leaf salad, curries, and a warm neighborhood atmosphere.
Moderate for the Washington area. Meals and coffee are manageable, but hotels and upscale dining can be pricey.
Tip 18-20% at restaurants. Tip USD 1-2 per drink at bars, round up taxis, and tip hotel staff USD 2-5. Tipping is not usually expected for counter service.
Find answers to the most common questions about traveling from Chicago, IL to Silver Spring, MD 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 Silver Spring, MD, this guide helps you travel smarter and with confidence.

Most Chicago, IL to Silver Spring, MD flights use the O'Hare International Airport to Baltimore/Washington International Airport airport pair. Use this guide to compare Chicago, IL and Silver Spring, MD airports on this route, check city-centre transport, alongside checking practicalities like airport facilities and services.
O'Hare International Airport is 3 km from Chicago city centre. Public transport options include:
O'Hare International Airport has practical services for this route, including Wifi, Shopping, Parking, Dining, ATM, Taxis, Accessibility, WC, Hotel, Shower, Lounge, Lost and Found Office, and Car Rental.
Food options include: Restaurants are located in all terminals, offering a variety of cuisines including American and intertiol. Top options include Tortas Frontera and Publican Tavern.
Free Wi-Fi available throughout the airport. ATMs are located throughout all terminals.
Lost and found is available at the station.
Available at O'Hare International Airport: Parking, Taxis, WC.
Available at O'Hare International Airport: Car Rental.
Accessibility facilities are available at O'Hare International Airport: Elevators, ramps, toilets.
Nearby hotels include Hotels such as Hilton Chicago O'Hare are located on airport grounds, with others like the Hyatt Regency nearby..
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