Old Town Chicago Travel Guide
Tourist Guide
Visit Old Town Chicago
Popular places to visit
Wrigley Field
A big piece of Chicago's soul, an ancient stadium that keeps alive the quirky, edgy madness of baseball.
Naval Base Great Lakes
After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.
Michigan Avenue
You can find the perfect gifts to bring home when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.
McCormick Place
Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.
Navy Pier
One of Chicago’s most popular attractions, especially on a hot day, with its fun fair, boats, circus and theatre.
Millennium Park
See mind-bending sculptures, a musically-inspired lawn and giant water fountains that double-up as video screens.
Activities
Skydeck - Willis Tower Admission
Chicago Sightseeing River and Lake Cruise
Chicago By Night River and Lake Cruise
Our pick of the best Old Town Chicago Hotel Deals
Congress Plaza Hotel
"Great location and clean"
Reviewed on 29 May 2026
Hotel Riu Plaza Chicago
"Staff was super nice and attentive."
Reviewed on 29 May 2026
The Chicago Hotel Collection - Magnificent Mile
"rooftop"
Reviewed on 29 May 2026
Hyatt Regency O'Hare Chicago
"Good location if you want good dining options, close to the airport, feels safe to walk around outside, area is pretty good."
Reviewed on 29 May 2026
Fairmont Chicago at Millennium Park
"We really enjoyed our stay at this beautiful hotel! The hotel was extremely clean and the rooms were large and well designed. The amenities were top notch. The front desk staff were extremely knowledgeable and helpful. You can walk to any of the top attractions from this hotel and we put on 9 miles ..."
Reviewed on 29 May 2026
The Chicago Hotel Collection Ambassador Gold Coast
"Fantastic location Great space Wonderful atmosphere"
Reviewed on 30 May 2026
Other neighbourhoods around Old Town Chicago
Near North Side
Known for its fascinating museums, panoramic lake views and popular shops, there's plenty to explore in Near North Side. Top attractions like Michigan Avenue and Navy Pier are major draws. Catch the metro at Clark-Division Station or Chicago Station (Brown Line) to see more of the city.
Lincoln Park
Known for its ample dining options and fantastic lake views, there's plenty to explore in Lincoln Park. You can visit top attractions like Lake Michigan and Lincoln Hall, and jump on the metro at Fullerton Station or Armitage Station to see more of the city.
River North
Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.
Magnificent Mile
Are you interested in fascinating museums, panoramic lake views and popular shops? A visit to Magnificent Mile might be the perfect thing. You can also explore top sights like Michigan Avenue and Chicago Water Tower.
Streeterville
Michigan Avenue and Navy Pier are just a few worthwhile attractions to visit in Streeterville. Travellers also love the fascinating museums, panoramic lake views and popular shops.
Downtown Chicago
Known for its fascinating museums, stunning river views and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Michigan Avenue and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.
