Old Town Chicago Travel Guide

Chicago

Photo by trenton.badillo
Photo by trenton.badillo
Photo by Marc Jacobs
Photo by Marc Jacobs
Photo by Lisa Frackiewicz
Photo by Lisa Frackiewicz
Photo by Joy Taylor
Photo by Joy Taylor
Photo by Rita Irvine
Photo by Rita Irvine

Popular places to visit

Wrigley Field featuring a city, a sporting event and city views

Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Navy Pier

Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier
Magnificent Mile - River North which includes street scenes, signage and night scenes

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.

Michigan Avenue
McCormick Place

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.

McCormick Place
Millennium Park which includes autumn colours, modern architecture and street scenes

Millennium Park

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Millennium Park
Soldier Field which includes a high-rise building, a city and modern architecture

Soldier Field

Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.

Soldier Field

Things to do

Workers Cottages of Oldtown Triangle Walking Tour

Workers Cottages of Oldtown Triangle Walking Tour

฿1,460
per adult
Workers Cottages of Oldtown Triangle Walking Tour
River tour boat in Chicago

Architecture River Tour

฿1,345
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

฿1,314
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

฿1,460
per adult
94% of travellers recommend
Chicago By Night River & Lake Cruise
Chicago: Architecture Boat Tour with Drinks

Chicago: Architecture Boat Tour with Drinks

฿1,363
per adult
86% of travellers recommend
Chicago: Architecture Boat Tour with Drinks
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

฿797
per adult
86% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
See all activities in Chicago

Top hotels in Old Town Chicago

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
The price is ฿5,745 per night from 4 Aug to 5 Aug
฿5,745
฿6,744 total
4 Aug - 5 Aug
includes taxes & fees
Stay at this business-friendly hotel in Chicago. Enjoy free Wi-Fi, 2 restaurants and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
7.8/10 Good! (8,992 reviews)
"Hotel was beautiful"

Reviewed on 27 Jul 2025

Congress Plaza Hotel
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
505 N Michigan Ave, Chicago, IL
The price is ฿7,903 per night from 22 Aug to 23 Aug
฿7,903
฿10,313 total
22 Aug - 23 Aug
includes taxes & fees
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free Wi-Fi, 2 restaurants and breakfast (surcharge). Our guests praise the pool and the helpful staff in ...
9/10 Wonderful! (2,129 reviews)
Overall a great family hotel
"Great time in Chicago and the hotel made it phenomenal! It’s in a very central location and allows access to all the major tourist attractions within walking distance. We really enjoyed Saturday movie night at the pool!"

Reviewed on 28 Jul 2025

InterContinental Chicago Magnificent Mile by IHG
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl, Chicago, IL
The price is ฿4,653 per night from 17 Aug to 18 Aug
฿4,653
฿5,462 total
17 Aug - 18 Aug
includes taxes & fees
Stay at this business-friendly hotel in Chicago. Enjoy a fitness centre, valet parking (surcharge) and a 24-hour front desk. Our guests praise the helpful staff ...
8.8/10 Excellent! (2,548 reviews)
"Great area, clean hotel but, parking is expensive. There was no pool."

Reviewed on 27 Jul 2025

Hilton Chicago/Magnificent Mile Suites
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street, Chicago, IL
The price is ฿5,182 per night from 24 Aug to 25 Aug
฿5,182
฿6,083 total
24 Aug - 25 Aug
includes taxes & fees
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy free Wi-Fi, breakfast (surcharge) and a fitness centre. Our guests praise the helpful staff in ...
8.8/10 Excellent! (1,319 reviews)
"Great location. Very walkable to restaurants and bars. Not far from Michigan Ave, very quick Uber ride or about a 25 - 30 minute walk. The hotel is very good with very friendly staff. Its clean, but our room was showing some wear and tear. There was some minor mold in ine corner of the tub, the bed ..."

Reviewed on 28 Jul 2025

Crowne Plaza Chicago West Loop by IHG
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
The price is ฿5,334 per night from 24 Aug to 25 Aug
฿5,334
฿6,261 total
24 Aug - 25 Aug
includes taxes & fees
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service and a fitness centre. Our guests praise the breakfast and the pool in their reviews. ...
8.4/10 Very Good! (4,568 reviews)
"Close to everything l"

Reviewed on 27 Jul 2025

Embassy Suites by Hilton Chicago Downtown River North
citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
80 East Wacker Place, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ฿5,065 per night from 26 Aug to 27 Aug
฿5,065
฿5,946 total
26 Aug - 27 Aug
includes taxes & fees
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free Wi-Fi, breakfast (surcharge) and a fitness centre. Our guests praise the breakfast and the ...
9.2/10 Wonderful! (3,457 reviews)
"My stay was good, although at the time of my arrival my room that was assigned to me was not working, couldn't take a shower after a long day, thankfully it was fix the following day, had to go to a friends house to take a shower, overall my stay was good."

Reviewed on 26 Jul 2025

citizenM Chicago Downtown
See all 4,566 properties in Old Town Chicago
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other neighbourhoods around Old Town Chicago

Chicago featuring a city and modern architecture

Lincoln Park

5/5(5 area reviews)

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.

Lincoln Park
Gold Coast which includes street scenes as well as a couple

Gold Coast

The ample dining options and fantastic lake views are top of the list for many visitors to Gold Coast. A stop by Michigan Avenue or Lake Michigan might round out your trip.

Gold Coast
Magnificent Mile - River North which includes street scenes, signage and night scenes

Near North Side

4.5/5(248 area reviews)

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.

Near North Side
Default Image

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.

River North
Magnificent Mile - River North

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.

Magnificent Mile
Navy Pier which includes wild flowers and general coastal views as well as a couple

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.

Streeterville

Old Town Chicago Travel Guide