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Deals on vacations and trips to Grand Boulevard
Grand Boulevard flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
![Virgin Hotels Chicago](https://images.trvl-media.com/lodging/10000000/9120000/9119600/9119528/63f8ab3d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Virgin Hotels Chicago
Downtown Chicago
Save 100% on your flight
per person
Aug 14 - Aug 17
found 4 hours ago
Roundtrip flight included
Jacksonville (JAX) to Chicago (ORD)
A nightclub, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the a rooftop terrace, bar/lounge, and limo/town car service.
![The Peninsula Chicago](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/f1144862_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
The Peninsula Chicago
Downtown Chicago
Save 100% on your flight
per person
Aug 14 - Aug 17
found 4 hours ago
Roundtrip flight included
Jacksonville (JAX) to Chicago (ORD)
A full-service spa, 2 restaurants, and an indoor pool are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities and babysitting. Enjoy the gym and perks like free WiFi.
![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/425695dc_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
per person
Aug 14 - Aug 17
found 4 hours ago
Roundtrip flight included
Jacksonville (JAX) to Chicago (ORD)
A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and in-room childcare. Enjoy the gym and perks like free WiFi.
![Park Hyatt Chicago](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/3226e31b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Park Hyatt Chicago
Downtown Chicago
Save 100% on your flight
per person
Aug 14 - Aug 17
found 4 hours ago
Roundtrip flight included
Jacksonville (JAX) to Chicago (ORD)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this eco-certified hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the indoor pool, bar/lounge, and laundry facilities.
![Millennium Knickerbocker Chicago](https://images.trvl-media.com/lodging/1000000/20000/15100/15087/cf5ebf5d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Millennium Knickerbocker Chicago
Downtown Chicago
Save 100% on your flight
per person
Aug 1 - Aug 4
found 1 hour ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. Self parking, a library, and express check-in are also offered.
Top Grand Boulevard hotels deals
![Congress Plaza Hotel](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/41255425_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $161 per night
$161
per night
Jul 1 - Jul 2
This smoke-free hotel's 2 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a coffee shop, and a hair salon are also offered.
Free WiFi
Restaurant
![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/1676cf3d_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $167 per night
$167
per night
Jun 30 - Jul 1
This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and free full breakfast each morning. Valet parking, a business center, and a grocery/convenience store are also offered.
Pool
Breakfast included
![River Hotel](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/a97325e3_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
River Hotel
75 East Wacker Drive, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $152 per night
$152
per night
Jun 30 - Jul 1
A restaurant and a gym are featured at this hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Express check-in, express check-out, and dry cleaning are also on offer.
Pet friendly
Free WiFi
![Eurostars Magnificent Mile](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/5dc4c553_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Eurostars Magnificent Mile
660 North State Street, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $180 per night
$180
per night
Jul 2 - Jul 3
A full-service spa and a gym are featured at this boutique hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a sauna on site, and a 24-hour front desk and express check-out are also provided.
Spa
Free WiFi
![The Westin Michigan Avenue Chicago](https://images.trvl-media.com/lodging/1000000/30000/21100/21055/f5c69379_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
The Westin Michigan Avenue Chicago
909 North Michigan Ave, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $146 per night
$146
per night
Jul 11 - Jul 12
A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the gym, bar/lounge, and coffee shop.
Spa
Pet friendly
![Hotel Felix River North/Magnificent Mile](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/f8a6a426_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Hotel Felix River North/Magnificent Mile
111 W Huron St, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $119 per night
$119
per night
Jun 30 - Jul 1
This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Self parking, a lobby fireplace, and a communal living room are also offered.
Pet friendly
Free WiFi
Don't see what you're looking for?
See all available properties in Grand Boulevard
View all propertiesLowest 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.
Popular places to visit
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Dr. Daniel Hale Williams Residence
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Photos of local treasures
Browse Grand Boulevard vacation photos for more inspiration