Old Town Chicago Travel Guide

Tourist Guide

A coastal cityscape with a marina, high-rise buildings, and a river.
A city skyline with a prominent skyscraper, a waterfront, and a curved road.
A black and white sign with ornate metalwork and the words "OLD TOWN" prominently displayed.

Stay near popular Old Town Chicago attractions

Second City

9.6/10 (15 reviews)
You can make plans for a show at Second City on your trip to Chicago. Amble around this vibrant area's lakeside or experience its entertainment choices.
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Activities

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

NZ$47
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

NZ$42
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Art Institute of Chicago

Art Institute of Chicago

NZ$69
per adult
92% of travellers recommend
Art Institute of Chicago
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

NZ$70
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Flyover in Chicago

Flyover in Chicago

NZ$54
per adult
96% of travellers recommend
Flyover in Chicago
See Chicago's magnificent skyline at night!

Chicago 3D Fireworks Cruise

NZ$90
per adult
72% of travellers recommend
Chicago 3D Fireworks Cruise
See all activities in Chicago

Our pick of the best Old Town Chicago Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
The price is NZ$213 per night from 8 Sept to 9 Sept
NZ$213
8 Sept - 9 Sept
includes taxes & fees
Stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
8/10 Very good! (10,288 reviews)
"Lower price$"

Reviewed on 11 Aug 2026

Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
The price is NZ$289 per night from 30 Aug to 31 Aug
NZ$289
30 Aug - 31 Aug
includes taxes & fees
Stay at this business-friendly hotel in Chicago. Enjoy free Wi-Fi, a 24-hour fitness centre and valet parking (surcharge). Our guests praise the helpful staff ...
The Chicago Hotel Collection Ambassador Gold Coast
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
The price is NZ$458 per night from 11 Sept to 12 Sept
NZ$458
11 Sept - 12 Sept
includes taxes & fees
Stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge) and a free airport shuttle. Our guests praise the helpful staff and ...
Hilton Chicago O'Hare Airport
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
171 W Randolph St Chicago IL
The price is NZ$416 per night from 10 Sept to 11 Sept
NZ$416
10 Sept - 11 Sept
includes taxes & fees
Stay at this business-friendly hotel in Chicago. Enjoy free Wi-Fi, breakfast (surcharge) and a 24-hour fitness centre. Our guests praise the helpful staff and ...
9/10 Wonderful! (2,763 reviews)
"Very good location. The bar was very good too."

Reviewed on 11 Aug 2026

The Allegro Royal Sonesta Hotel Chicago Loop
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
The price is NZ$327 per night from 30 Aug to 31 Aug
NZ$327
30 Aug - 31 Aug
includes taxes & fees
Stay at this business-friendly hotel in Rosemont. Enjoy free Wi-Fi, breakfast (surcharge) and a free airport shuttle. Our guests praise the helpful staff and ...
8.8/10 Excellent! (3,004 reviews)
"The Hyatt is a perfect place to enjoy Chicago is you want to stay close to the airport. Public transportation is close and easily accessible, the hotel is immaculately cleaned, and the staff helped in every way possible. I definitely recommend this hotel"

Reviewed on 11 Aug 2026

Hyatt Regency O'Hare Chicago
Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago

4 out of 5
2233 S Martin Luther King Dr Chicago IL
The price is NZ$425 per night from 1 Sept to 2 Sept
NZ$425
1 Sept - 2 Sept
includes taxes & fees
Stay at this business-friendly hotel in Chicago. Enjoy free Wi-Fi, 3 restaurants and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
9.2/10 Wonderful! (1,256 reviews)
"Very nice, new room with excellent views of the city and Lake. Stayed for a concert at Soldier Field and it was an easy walk. Would stay again."

Reviewed on 11 Aug 2026

Hyatt Regency McCormick Place Chicago
See all 4,461 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.

Our guide on where to stay in Old Town Chicago

Find the best Old Town Chicago areas for the activities you enjoy most.
A busy city street with tall buildings, a bus, and cars.

Downtown Chicago

Known for its fascinating museums, stunning river views and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Navy Pier and Lake Michigan are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

A river with yellow boats, a bridge, and tall buildings.

The Loop

Lake Michigan and Michigan Avenue are a few top attractions in The Loop. Hop around the city on the metro at Washington Station or Lake Station and check out the area's fascinating museums, popular shops and acclaimed art galleries.

A historic castle-like building with intricate stonework and a paved walkway.

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.

A city street with a train passing overhead, cars, pedestrians, and a red brick building.

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.

The Chicago Theatre with illuminated marquee and a wet street reflecting lights.
Photo by Mattyboy876
Open Photo by Mattyboy876

Theatre District

While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more of the city at Washington Station or Monroe Station (Blue Line).

Old Town Chicago Travel Guide

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