Is it better to fly to O'Hare or Midway?

Midway is often faster to get out of, while O'Hare has more flight options.

Is the 'L' train easy to use?

Yes, it is the most efficient way to get around the city.

Do I need a car in Chicago?

No, public transit is excellent and parking is expensive.

What is the best time to visit?

Summer is vibrant, but autumn is also very pleasant.

Brookline

Chicago

Flight

Brookline to Chicago

Updated: 28 May 2026

The journey from Brookline to Chicago covers 1,500 kilometers. The most practical and fastest way to travel is by flight from Boston Logan International Airport to either O'Hare (ORD) or Midway (MDW) airports. The flight time is approximately 2.5 hours. Chicago is well-served by the 'L' train system, making it easy to reach the city center from either airport. Driving is possible but takes about 16-18 hours.

Total Distance: 1,500 km driving, 1,350 km air distance.

Fastest Way

Direct flight from Logan Airport to Chicago, taking 2.5 hours.

Cheapest Way

Direct flight booked in advance via budget airlines.

Compare Brookline to Chicago Routes

Flight

Direct

Duration

2 hours 30 mins

Avg Price

$120 - $300

Operator

United or American Airlines

Route

BOS to ORD or MDW

O'Hare is larger, while Midway is often closer to downtown.

Travel Tips

Airport Transit
Use the CTA Blue Line from O'Hare or the Orange Line from Midway to reach downtown.
Weather
Chicago is known as the 'Windy City'; pack layers, especially in winter.
Dining
Try the famous Chicago-style deep-dish pizza at local favorites like Lou Malnati's.
Booking
Book flights at least 21 days in advance for the best rates.
Walking
Chicago's downtown is very walkable, but use the 'L' for longer distances.

Safety Tips

General Safety
Stay in well-populated areas, especially at night.
Transit Safety
The CTA is generally safe, but keep your belongings close in crowded trains.
Emergency
Chicago has a comprehensive emergency response system; dial 911.
Awareness
Be aware of your surroundings when using your phone in public.