Search Hotels with Entertainment in Chicago

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Chicago Hotels with Entertainment

Top Chicago Hotels with Entertainment

Palmer House a Hilton Hotel
Relax in a comfortable seating area with a plush armchair and enjoy the warm ambiance of candles and a vase of flowers.

Palmer House a Hilton Hotel

4.0 star property
8.4 out of 10, Very good, (1792)
"Love this hotel"
The price is ₹14,881
₹19,614 total
includes taxes & fees
5 Aug - 6 Aug
Palmer House a Hilton Hotel
The Allegro Royal Sonesta Hotel Chicago Loop
Located on a busy street, the Hotel Allegro features a classic architectural design with a prominent marquee sign at the entrance.

The Allegro Royal Sonesta Hotel Chicago Loop

4.0 star property
8.8 out of 10, Excellent, (1856)
"We loved the location & the friendliness of the staff!"
The price is ₹14,537
₹19,816 total
includes taxes & fees
27 Jul - 28 Jul
The Allegro Royal Sonesta Hotel Chicago Loop
Hampton Inn Majestic Chicago Theatre District
Stunning historic theatre with ornate details and a grand entrance.

Hampton Inn Majestic Chicago Theatre District

3.0 star property
9.0 out of 10, Wonderful, (1002)
"Nice location and good bfast."
The price is ₹15,268
₹17,923 total
includes taxes & fees
27 Jul - 28 Jul
Hampton Inn Majestic Chicago Theatre District
Cambria Hotel Chicago Loop - Theatre District
Enjoy a comfortable stay in this stylish room featuring a dining area, seating area, and refrigerator.

Cambria Hotel Chicago Loop - Theatre District

4.0 star property
8.8 out of 10, Excellent, (1367)
"Very good location, clean and friendly staff"
The price is ₹15,393
₹18,069 total
includes taxes & fees
10 Aug - 11 Aug
Cambria Hotel Chicago Loop - Theatre District
The Royal Sonesta Chicago Downtown
Enjoy intimate dining or social gatherings on our rooftop terrace with elegant seating arrangements and a stunning city view.

The Royal Sonesta Chicago Downtown

4.0 star property
9.2 out of 10, Wonderful, (2710)
"Great location and beautiful hotel "
The price is ₹16,729
₹22,388 total
includes taxes & fees
17 Aug - 18 Aug
The Royal Sonesta Chicago Downtown
theWit Chicago, a Hilton Hotel
Experience the city from our spacious lobby with a stunning view, featuring a comfortable seating area and a vibrant floral arrangement.

theWit Chicago, a Hilton Hotel

4.5 star property
9.0 out of 10, Wonderful, (1001)
"Close to the sites we were going to and the price was reasonable."
The price is ₹22,573
₹29,021 total
includes taxes & fees
17 Aug - 18 Aug
theWit Chicago, a Hilton Hotel
Pendry Chicago
Relax in style with a panoramic view of the city from our rooftop lounge, featuring a deck and comfortable seating.

Pendry Chicago

4.5 star property
9.4 out of 10, Exceptional, (1023)
"Nice hotel, centrally located"
The price is ₹18,908
₹25,727 total
includes taxes & fees
11 Aug - 12 Aug
Pendry Chicago
Virgin Hotels Chicago
Relax on the rooftop with a mix of seating options and potted plants, overlooking a historic building and modern skyscrapers.

Virgin Hotels Chicago

4.5 star property
9.2 out of 10, Wonderful, (1344)
"Very well appointed rooms and wonderful customer service!!"
The price is ₹22,689
₹29,157 total
includes taxes & fees
24 Jul - 25 Jul
Virgin Hotels Chicago
Staypineapple, An Iconic Hotel, The Loop
Stunning interior space with ornate iron gates, marble panels, and a patterned rug.

Staypineapple, An Iconic Hotel, The Loop

4.0 star property
9.4 out of 10, Exceptional, (1002)
"Beautiful hotel in a great location."
The price is ₹17,713
₹23,311 total
includes taxes & fees
20 Jul - 21 Jul
Staypineapple, An Iconic Hotel, The Loop
Hyatt Regency Chicago
2 bars/lounges

Hyatt Regency Chicago

4.0 star property
9.2 out of 10, Wonderful, (3281)
"Great location and stay"
The price is ₹20,016
₹26,020 total
includes taxes & fees
6 Aug - 7 Aug
Hyatt Regency 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.