Is the train ride scenic?

Yes, especially through the Berkshires and along the Great Lakes.

How do I get to downtown from O'Hare?

The Blue Line train is the most cost-effective method.

Is Chicago safe for tourists?

Yes, tourist areas are generally safe with standard precautions.

What is the best time to visit?

Summer offers the best weather for lakefront activities.

No, Chicago has an extensive public transportation network.

Watertown

Chicago

Train Flight

Watertown to Chicago

Updated: 28 May 2026

Traveling from Watertown to Chicago covers roughly 1,000 miles. The most efficient method is a direct flight from Boston Logan to O'Hare or Midway. Alternatively, the Amtrak Lake Shore Limited offers a scenic overnight rail journey from Boston South Station. Driving takes approximately 16 hours via I-90 West through New York and Ohio. Chicago serves as a major hub for both rail and air travel in the United States.

Total Distance: 1,600 km driving, 1,550 km air distance.

Fastest Way

Direct flight from BOS to ORD.

Cheapest Way

Amtrak coach seat if booked well in advance.

Compare Watertown to Chicago Routes

	Train Direct	Flight Direct
Duration	22 hours	2 hours 45 mins
Avg Price	$130-$350	$150-$400
Operator	Amtrak Lake Shore Limited	United Airlines
Route	Boston South Station to Chicago Union Station.	BOS to ORD.
Tip	Book a roomette for a more comfortable overnight experience.	Take the Blue Line 'L' train from O'Hare directly to downtown Chicago.

Travel Tips

Ventura Card
Use a Ventra card for all CTA buses and trains in Chicago.
Windy City
Pack layers as the wind off Lake Michigan can make temperatures drop quickly.
Deep Dish
Try authentic deep-dish pizza at local institutions like Lou Malnati's.
Architecture
Take an architecture river cruise to see the city's famous skyline.
Airport
O'Hare is large; allow extra time for navigating terminals.

Safety Tips

Neighborhoods
Stick to well-lit, populated areas in the downtown and tourist districts.
Public Transit
Stay aware of your surroundings on the 'L' trains, especially late at night.
Scams
Be wary of strangers asking for money or offering unsolicited help.
Emergency
Call 911 for immediate assistance in any dangerous situation.