Is it better to fly or take the train?

Flying is much faster and often cheaper; the train is for those who enjoy the journey.

Which airport is better?

O'Hare is larger with more flights, while Midway is closer to downtown.

Do I need a car in Chicago?

No, public transit is excellent and parking is very expensive.

What is the best time to visit?

Summer is vibrant, but autumn offers beautiful weather and fewer crowds.

Westbrook

Chicago

Train Flight

Westbrook to Chicago

Updated: 28 May 2026

Traveling from Westbrook, Connecticut to Chicago, Illinois covers nearly 900 miles. The most practical method is to drive to Bradley International Airport (BDL) and take a direct flight to O'Hare (ORD) or Midway (MDW), which takes about 2.5 hours in the air. Alternatively, you can take the train from New Haven to New York City and board the Lake Shore Limited for a scenic, albeit long, overnight journey. Chicago is a major cultural hub known for its architecture, deep-dish pizza, and lakefront parks.

Total Distance: 1,450 km driving distance; 1,250 km straight-line air distance.

Fastest Way

Flying is significantly faster, with a total travel time of about 5 hours including airport transit.

Cheapest Way

Flying from Bradley International Airport is often cheaper than the train if booked in advance.

Compare Westbrook to Chicago Routes

	Train Connecting	Flight Direct
Duration	20 hours	2 hours 30 mins
Avg Price	$180-$400	$150-$350
Operator	Amtrak (Lake Shore Limited)	United Airlines / American Airlines
Route	New Haven to NYC Penn Station, then direct to Chicago Union Station.	Bradley International Airport (BDL) to O'Hare (ORD).
Tip	Book a roomette for a comfortable overnight experience.	Book at least 3 weeks in advance to secure the best fares.

Travel Tips

Airport Transit
Use the 'L' train (Blue Line) to get from O'Hare to downtown Chicago quickly and cheaply.
City Pass
Consider buying a Chicago CityPASS to save on admission to major attractions.
Weather
Chicago is known as the Windy City; dress in layers regardless of the season.
Dining
Try authentic deep-dish pizza at local institutions like Lou Malnati's or Giordano's.
Safety
Stick to well-lit, populated areas in the downtown Loop and River North districts.

Safety Tips

Public Transit
Stay aware of your surroundings when using the 'L' train late at night.
Pedestrian Safety
Chicago drivers can be aggressive; always use crosswalks and wait for the signal.
Emergency
Dial 911 for any emergency; the city has a robust police presence in tourist areas.
Valuables
Keep your belongings secure in crowded tourist spots like Navy Pier to prevent pickpocketing.