Is the train ride scenic?

Yes, the route through the Berkshires and along the Erie Canal is very picturesque.

How far is O'Hare from downtown?

It is approximately 18 miles, taking 45-60 minutes by train or car.

Do I need a car in Chicago?

No, Chicago has an excellent public transit system including trains and buses.

What is the best time to visit?

Late spring and early autumn offer the most comfortable temperatures.

Are there direct flights from Bridgeport?

No, you must use Bradley International (BDL) or airports in the NYC area.

Bridgeport

Chicago

Train Flight

Bridgeport to Chicago

Updated: 28 May 2026

The journey from Bridgeport to Chicago spans roughly 950 miles across the Northeast and Midwest. The most iconic route is the Amtrak Lake Shore Limited, which departs from New York Penn Station and travels along the historic New York Central Railroad line. Alternatively, you can fly from Bradley International Airport (BDL) near Hartford for a direct connection to O'Hare. Driving involves taking I-84 to I-80, crossing through Pennsylvania, Ohio, and Indiana.

Total Distance: Driving distance 1,530 km; straight-line air distance 1,300 km.

Fastest Way

Flight from BDL to ORD, taking approximately 2.5 hours in the air.

Cheapest Way

Flight from BDL to ORD, often cheaper than train sleeper accommodations.

Compare Bridgeport to Chicago Routes

	Train Connecting	Flight Direct
Duration	20 hours	2 hours 30 mins
Avg Price	$130 - $350	$120 - $300
Operator	Amtrak Lake Shore Limited	United Airlines
Route	Bridgeport to NYC Penn Station, then direct to Chicago Union Station.	Bradley International (BDL) to O'Hare (ORD).
Tip	Book a Viewliner sleeper car to enjoy the scenic Mohawk River Valley.	O'Hare is connected to downtown Chicago via the Blue Line 'L' train.

Travel Tips

Train Station
Chicago Union Station is centrally located and walkable to many downtown hotels.
Airport Transit
The Blue Line train from O'Hare is the most cost-effective way to reach downtown.
Weather
Chicago is known as the Windy City; pack layers even in the summer months.
Booking
Use the Amtrak website to check for 'Saver' fares on the Lake Shore Limited.
Dining
Try deep-dish pizza at a local institution like Lou Malnati's.

Safety Tips

Urban Awareness
Stay in well-lit, populated areas when exploring downtown at night.
Public Transit
Keep your belongings secure while riding the CTA trains and buses.
Driving
If driving, be prepared for heavy traffic on the I-80/I-90 toll roads.
Emergency
Dial 911 for any immediate emergencies while in the city.