Chicago Travel Guide

Chicago Summary


  • World-class museums
  • Beautiful architecture and well-preserved 19th century buildings
  • Reliable public transportation
  • Grant Park, Millennium Park and the Art Institute of Chicago
  • Great cuisine -- especially the pizza!
  • Shopping options -- from local shops to luxury boutiques
  • Vibrant nightlife and excellent comedy and blues shows
  • Free trolleys during the summer months and in weekends in fall and spring


  • Steep hotel prices
  • Hotels often booked up because of year-round conventions
  • Expensive taxis, with surcharges for everything
  • Crowds during the busy summer tourist season
  • Some areas not safe at night, though crime rates are dropping
  • Sprawling city makes walking not always practical
  • Pricey parking
  • Icy winters and year-round windy weather

Neighborhood Guides

  • Magnificent Mile: High-end boutiques and some of the city’s best hotels and restaurants
  • Gold Coast: Victorian townhouses, expensive shops and celebrity-spotting restaurants, but also trendy bars, nightclubs and historical places dating back to the 1890s
  • River North: Bustling and affluent neighborhood with luxury hotels, great restaurants and a thriving art scene
  • The Loop: Chicago's business district, but also home to the Theatre District, major cultural institutions (like the Art Institute of Chicago), historic buildings and famous parks
  • South Loop: Mansions, well-preserved historical landmarks and a diverse dining and nightlife scene
  • Lakeview: A dining, shopping and entertainment hotspot that's home to Chicago's gay nightlife scene and Wrigley Field
  • Lincoln Park: Historic neighborhood with an abundance of museums, boutiques and restaurants
  • Near West Side: Multi-ethnic and student neighborhood adjacent to The Loop. It's home to restaurants, bars and the United Center arena.

What It's Like

Even on its infamous windy winter days, Chicago has a lot to offer travelers. World-class museums, great parks, top-notch dining and shopping, and cutting-edge architecture make Chicago one of the most fascinating cities in the midwest. Conventions are perennial in the Windy City, so upscale dining and accommodation options abound -- but cheaper alternatives (though don't expect bargains) can also be found.

After the 1871 Great Fire, whole neighborhoods had to be literally raised from the ashes, and most of those original late-19th century buildings still remain. Nowadays, these old constructions sit side by side with modern shimmering towers, high-end boutiques and acclaimed restaurants. Beautiful architecture -- new and old -- is present in many areas, like the Gold Coast, Old Town and the South Loop, but its historic feeling has a surprisingly natural way of blending in to diverse, vibrant neighborhoods like Pilsen and Boystown.

Where to Stay

The Windy City has some 700 hotels with more than 100,000 rooms available, but it is mandatory to book well in advance because of the ever-present conventions. Chicago is not known for its cheap rooms, but you are likely to have plenty of attractions and great dining options nearby no matter where you stay.

The Loop, Chicago's commercial center, is one of the most popular places to stay: Many tourist attractions are within walking distance, and it's well connected to the rest of the city by public transportation. But don’t expect to find cheap lodging here.

To the north of The Loop, on the other side of the Chicago River, is an iconic stretch of North Michigan Avenue known as the Magnificent Mile, home to many of the city's most upscale hotels and shops. The hotels in River North, to the east of the Magnificent Mile (and still within walking distance), tend to be slightly more affordable.

Hotels are scarcer farther to the north, in Lincoln Park or Lakeview, or on the South Side. But you'll likely pay a lot less than if you stayed closer to the tourist sites.


View all Chicago Hotels


Languages: English
Airports: O'Hare International Airport
Midway Airport
Peak: April - June
Off-Peak: Jan. - March
Visa: No, for nationalities included in the Visa Waiver Program
Vaccines: No
Currency: U.S. Dollar
Electricity: 120 V, 60 Hz
Tipping: 15-20% in restaurants and cabs

Oyster Travel Guides

Gold Coast Travel Guide
Gold Coast Travel Guide
The posh Gold Coast is a popular tourist destination, especially during the warmer months. Well-preserved… Read More
Lakeview Travel Guide
Lakeview Travel Guide
Eclectic and lively are the two words that best describe Lakeview. The neighborhood is a… Read More
Lincoln Park Travel Guide
Lincoln Park Travel Guide
Lincoln Park is a residential neighborhood north of the Old Town and directly west of… Read More
Magnificent Mile Travel Guide
Magnificent Mile Travel Guide
The Magnificent Mile, an iconic stretch of North Michigan Avenue, is the heart of Chicago's… Read More
Oak Brook Travel Guide
This small suburban area, located 21 miles (a 35-minute drive) from downtown Chicago, is a… Read More
River North Travel Guide
Art galleries, restaurants, nightclubs, upscale retail shops -- there’s a lot of everything for everyone… Read More
South Loop Travel Guide
South Loop Travel Guide
The South Loop neighborhood is an area east of the Chicago River and south of… Read More
Streeterville Travel Guide
Streeterville Travel Guide
Streeterville is one of Chicago's most affluent neighborhoods, with renowned restaurants and luxurious condos lining… Read More
The Loop Travel Guide
The Loop, the city's main business district, is the heart of downtown Chicago. Here, looming… Read More

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