- Recommended
Stamford History Center
Stamford's leading local history museum covers the city's colonial, industrial, and social past through changing exhibitions and archives.
Flights from Chicago, IL to Stamford, CT depart on average 95 times per day, taking around 2h 27m. Cheap flight tickets for this journey start at $191 (€154) but you can travel from only $131 (€105) by bus.
There are 42 flights per day. The earliest flight runs at 05:00, the last at 23:05. The fastest flight covers the 731 miles (1178 km) distance in 2h 27m. March is the cheapest month to fly.
Distance 731 miles (1178 km) |
Average flight duration 2h 27m |
Cheapest ticket price $191 (€154) |
Flights per day 95 |
Direct flights 42 |
Fastest flight 2h 27m |
First flight 5:00 AM |
Last flight 11:05 PM |
Cheapest Month Mar |
Cheapest Day Thu |
High Season Jan - Mar |
Low Season Apr - Jun |
Best time to book 49 days |
Omio recommends booking the bus as it is the most popular option from Chicago, IL to Stamford, CT among Omio's users. If you are prioritising price, take the bus, with an average ticket price of $131 For those with little time, consider booking a flight, which has an average total journey time of 4h 27m. Average ticket prices depend on the travel mode: a bus costs an average of $131, while a train costs an average of $446.
Distance: 731 miles (1178 km)
| Flight | Most popular Bus | Train | Driving |
|---|---|---|---|
$191 Average price | $131 Average price Cheapest | $446 Average price | $171 Average price (fuel + tolls) |
4h 27m Average total duration Fastest 2h 27m Onboard + 2h 0m Additional time* | 22h 40m Average total duration 22h 10m Onboard + 30m Additional time* | 24h 59m Average total duration 24h 29m Onboard + 30m Additional time* | 12h 31m 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 Stamford, CT:
A bus is $60 (€49) less than a flight for this route with tickets for a flight from Chicago, IL to Stamford, CT costing on average $191 (€154).
A bus is $316 (€255) less than a train for this route with tickets for a train from Chicago, IL to Stamford, CT costing on average $446 (€360).
Other travel options to Stamford, CT take longer:
Bus takes on average 22h 10m.
Train takes on average 24h 29m.
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.
Discover the best of Stamford, CT — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Stamford, CT trip today.
Stamford's leading local history museum covers the city's colonial, industrial, and social past through changing exhibitions and archives.
A contemporary nonprofit gallery featuring regional and international artists, valued for ambitious exhibitions and creative programming.
This nature center includes educational exhibits on local wildlife and habitats, making it a family-friendly museum-style stop.
Stamford's signature waterfront park offers beaches, walking paths, a carousel, and broad Long Island Sound views for an easy escape.
A large urban park with gardens, trails, sports fields, and seasonal events, popular with both locals and families.
This downtown public square hosts concerts, markets, and winter skating, making it a lively gathering place year-round.
A thick Greek-style pizza with an oily, crisp crust and rectangular slices. A Connecticut classic common in local pizzerias and taverns.
A split hot dog topped with mustard, relish, onions and bacon or cheese. Popular in southern Connecticut for a quick local bite.
A lobster roll served warm with melted butter on a toasted bun. A signature Connecticut seafood dish enjoyed along the coast.
Established Italian restaurant popular for handmade pasta, seafood and elegant dining suited to special occasions.
Classic upscale steakhouse known for dry-aged beef, seafood and polished service in a refined downtown setting.
Lively modern Mexican restaurant and tequila bar known for tacos, guacamole and a stylish, energetic atmosphere.
More expensive than many U.S. cities. Hotels, dining, and parking are high; local transit is limited, so visitors often rely on Metro-North, rideshares, or taxis.
Tip 18-20% at restaurants, more for excellent service. Round up or tip 10-15% for taxis. Cafes often have tip jars or screen prompts for $1-2 or 10-15%.
Find answers to the most common questions about traveling from Chicago, IL to Stamford, CT 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 Stamford, CT, this guide helps you travel smarter and with confidence.

Most Chicago, IL to Stamford, CT flights use the O'Hare International Airport to Newark Liberty International Airport airport pair. Use this guide to compare Chicago, IL and Stamford, CT 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..
Here are some other resources that might have the information you need