Is there a direct flight to Chicago?

Yes, United Airlines offers direct flights from Bradley International Airport (BDL) to Chicago (ORD).

How long is the flight?

The flight time is approximately 2.5 hours.

What is the best way to get around Chicago?

The 'L' train system is the best option for exploring the city.

Are there trains to Chicago?

Yes, but it is a very long journey with multiple transfers.

Is Chicago safe for tourists?

The main tourist areas are generally safe, but always remain aware of your surroundings.

Waterford

Chicago

Train Flight

Waterford to Chicago

Updated: 28 May 2026

The distance from Waterford to Chicago is approximately 850 miles. The most practical way to travel is by flying from Bradley International Airport (BDL) in Hartford to O'Hare International Airport (ORD) or Midway International Airport (MDW), which takes about 2.5 hours in the air. Alternatively, you can take an Amtrak train, but it involves a long journey with transfers, taking over 20 hours. Chicago is a major cultural and economic hub with a rich history and numerous attractions. Plan your travel well in advance to secure the best flight prices.

Total Distance: 1,500 km driving distance; 1,300 km straight-line air distance.

Fastest Way

Flying is the fastest method, taking only a few hours compared to the long train journey.

Cheapest Way

Flying is often the most cost-effective and fastest way to reach Chicago from Connecticut.

Compare Waterford to Chicago Routes

	Train Connecting	Flight Direct
Duration	22 hours	2 hours 30 mins (flight time)
Avg Price	$200-$500	$150-$400
Operator	Amtrak	United Airlines
Route	New London to New York to Chicago.	Bradley International Airport (BDL) to O'Hare International Airport (ORD).
Tip	This is a very long journey; consider a sleeper car for comfort.	Book your flight at least a month in advance for the best rates.

Travel Tips

Airport Access
Bradley International Airport is about an hour drive from Waterford.
Chicago Transit
The 'L' train system is a convenient way to get around the city center.
Book Flights Early
Flight prices fluctuate; use price tracking tools to find the best deals.
Car Rental
Renting a car is not necessary if you plan to stay in the city center.
Local Food
Don't miss out on trying some authentic Chicago-style deep-dish pizza while you are in town.

Safety Tips

Stay in Tourist Areas
Stick to well-populated areas, which are well-patrolled and tourist-friendly.
Traffic Awareness
Chicago traffic can be heavy during rush hour; plan your travel accordingly.
Secure Valuables
Keep your belongings secure in crowded tourist areas and on public transit.
Emergency Services
Chicago has a comprehensive emergency response system; dial 911 for assistance.