Anna and Frederick Douglass Park

Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$4,258, price is now S$2,932 per person
S$2,932
per person
9 Oct - 15 Oct
found 12 hours ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
9.4/10 Exceptional! (2,063 reviews)
Great view of the lake and city

Reviewed on 18 Aug, 2025

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$4,369, price is now S$2,983 per person
S$2,983
per person
9 Oct - 15 Oct
found 12 hours ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
9.4/10 Exceptional! (1,007 reviews)
Loved the hotel. Very clean and comfortable. The gentleman who checked us out was not the most friendly, but everyone else was super helpful!

Reviewed on 18 Aug, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$5,300, price is now S$3,680 per person
S$3,680
per person
9 Oct - 15 Oct
found 12 hours ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
This property is beautiful and located in a great area.

Reviewed on 19 Aug, 2025

Tours & day trips

See all 174 activities
Architecture River Tour

Architecture River Tour

Activity duration is 1 hour and 15 minutes
9.6 out of 10 with 1442 reviews
Free cancellation available
Price is S$63 per adult
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Food, drink & nightlife

See all 35 activities
Chicago: Architecture Boat Tour with Drinks

Chicago: Architecture Boat Tour with Drinks

Activity duration is 1 hour and 30 minutes
8.8 out of 10 with 17 reviews
Free cancellation available
Price is S$54 per adult
Chicago: Architecture Boat Tour with DrinksOpens in new tab

Private & custom tours

See all 32 activities
Eastside Chicago The Heist Exploration Game and Tour

Eastside Chicago The Heist Exploration Game and Tour

Activity duration is 1 hour and 35 minutes
Free cancellation available
The previous price was S$16 and current price is S$13 per adult*
Eastside Chicago The Heist Exploration Game and TourOpens in new tab

Attractions

See all 16 activities
360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

Activity duration is 30 minutes
8.4 out of 10 with 657 reviews
Free cancellation available
Price is S$39 per adult
360 CHICAGO Observation DeckOpens in new tab

Adventure & outdoor

See all 14 activities
Chicago White Sox Baseball Game at Guaranteed Rate Field

Chicago White Sox Baseball Game at Guaranteed Rate Field

Activity duration is 2 hours and 30 minutes
Price is S$18 per adult
Chicago White Sox Baseball Game at Guaranteed Rate FieldOpens in new tab

Popular places to visit

Garfield Park Conservatory featuring a park

Garfield Park

After visiting Garfield Park, make a plan to see the other sights and activities in Chicago. Discover the top-notch restaurants and acclaimed art galleries in this vibrant area.

Garfield Park
United Center

United Center

4.5/5(15 reviews)

Catch an event at United Center during your trip to Chicago. Amble around this vibrant area's lakeside or experience its entertainment choices.

United Center

Sinai Hospital

If Sinai Hospital is what brings you to town, hopefully you'll have a chance to explore more of Chicago.

Sinai Hospital

Mount Sinai Hospital

If Mount Sinai Hospital is what brings you to town, hopefully you'll have a chance to explore more of Chicago.

Mount Sinai Hospital

Mt. Sinai Hospital Medical Center

If Mt. Sinai Hospital Medical Center is what brings you to town, hopefully you'll have a chance to explore more of Chicago.

Mt. Sinai Hospital Medical Center

Sinai Health System

If Sinai Health System is what brings you to town, hopefully you'll have a chance to explore more of Chicago.

Sinai Health System

Top Anna and Frederick Douglass Park Hotel Deals

Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

2.5 out of 5
710 S Seeley Avenue, Chicago, IL
Hampton Inn & Suites Chicago Medical District UIC
Hotel Chicago West Loop, SureStay Collection by Best Western

Hotel Chicago West Loop, SureStay Collection by Best Western

2.5 out of 5
1622 W Jackson Blvd, Chicago, IL
Hotel Chicago West Loop, SureStay Collection by Best Western
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Congress Plaza Hotel
Cozy and Modern Stay in the Heart of C

Cozy and Modern Stay in the Heart of C

3 out of 5
1407 w 15th St Chicago, Chicago, IL
Cozy and Modern Stay in the Heart of C
The Neighborhood Hotel-Little Italy

The Neighborhood Hotel-Little Italy

4 out of 5
1431 W Taylor St, Chicago, IL
The Neighborhood Hotel-Little Italy
Courtyard by Marriott Chicago at Medical District/UIC

Courtyard by Marriott Chicago at Medical District/UIC

3.5 out of 5
625 South Ashland Avenue, Chicago, IL
Courtyard by Marriott Chicago at Medical District/UIC
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
Crowne Plaza Chicago West Loop by IHG
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
Palmer House a Hilton Hotel
Sonder by Marriott Bonvoy Market Hall Apartments West Loop

Sonder by Marriott Bonvoy Market Hall Apartments West Loop

3.5 out of 5
1436 West Randolph Street, Chicago, IL
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
See all 4,234 properties in Anna and Frederick Douglass Park
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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.