- 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 3h 21m. Cheap flight tickets for this journey start at $58 if you book in advance.
There are 43 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 0m. March is the cheapest month to fly.
Distance 731 miles (1178 km) |
Average flight duration 3h 21m |
Cheapest ticket price $58 |
Flights per day 95 |
Direct flights 43 |
Fastest flight 2h 0m |
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 |
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..
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