Old Town Chicago, IL

Chicago

This shows Lincoln Park, Diversey Harbor with its moored boats, Lake Michigan to the left and the skyline in summer. There is morning light on the city.
A city skyline with a prominent skyscraper, a waterfront, and a curved road.
Old Town Chicago Neighborhood entrance gate and sign

Stay near popular Old Town Chicago attractions

Second City

4.8/5 (15 reviews)
You can enjoy a show at Second City during your stay in Chicago. Amble around this vibrant area's lakeside or experience its entertainment choices.
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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 ￥21,756 per night from Jun 29 to Jun 30
￥21,756
￥25,867 total
Jun 29 - Jun 30
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
8/10 Very Good! (10,252 reviews)
"The only negative I had with the hotel was that their food choices were limited, and there were not a lot of healthy options. I would have really appreciated more veg choices with the meals, and more salad options."

Reviewed on Jun 12, 2026

Congress Plaza Hotel
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
The price is ￥23,098 per night from Jun 30 to Jul 1
￥23,098
￥27,463 total
Jun 30 - Jul 1
includes taxes & fees
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...
7.8/10 Good! (1,569 reviews)
"I"

Reviewed on Jun 12, 2026

The Chicago Hotel Collection - Magnificent Mile
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is ￥25,478 per night from Jun 28 to Jun 29
￥25,478
￥29,041 total
Jun 28 - Jun 29
includes taxes & fees
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
8.8/10 Excellent! (2,656 reviews)
"I really liked it and recommend it."

Reviewed on Jun 12, 2026

Hyatt Regency O'Hare Chicago
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
The price is ￥40,701 per night from Jul 3 to Jul 4
￥40,701
￥47,779 total
Jul 3 - Jul 4
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
8.4/10 Very Good! (2,337 reviews)
"Todo estuvo muy bueno"

Reviewed on Jun 11, 2026

Hilton Chicago O'Hare Airport
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 ￥25,047 per night from Jul 1 to Jul 2
￥25,047
￥29,777 total
Jul 1 - Jul 2
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
8.2/10 Very Good! (1,595 reviews)
"Filthy, dirty, hotel housekeeping services rundown needs paint attention. It was absolutely disgusting like being in the college dorm room."

Reviewed on Jun 12, 2026

The Chicago Hotel Collection Ambassador Gold Coast
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street Chicago IL
The price is ￥18,687 per night from Jul 5 to Jul 6
￥18,687
￥29,838 total
Jul 5 - Jul 6
includes taxes & fees
Stay at this hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8/10 Very Good! (3,102 reviews)
"I haven't stayed at a hotel/hostel before, so I don't know if my expectations were unreasonable. First, the good. The staff were friendly and helpful. The location was perfect. The hot water and AC were plentiful. I felt safe and wasn't bothered by noise from neighbors. I didn't see any bugs. They ..."

Reviewed on Jun 13, 2026

Freehand Chicago
See all 4,556 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.

Where to stay in Old Town Chicago

Find the best Old Town Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Old Town Chicago
Learn more about Old Town Chicago

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.

Magnificent Mile

Michigan Avenue and Chicago Water Tower are just a few worthwhile attractions to visit in Magnificent Mile. Travelers also love the fascinating museums, panoramic lake views, and popular shops.

The Loop

Michigan Avenue and Lake Michigan 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.

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.

Panoramic view of Lincoln Park and the Chicago skyline.

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.

Old Town Chicago, IL

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