Grand Boulevard Vacations from $356
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Your Grand Boulevard Vacation
Experience all the fabulous things this neighborhood has to offer with a customized Grand Boulevard vacation package. However you imagine spending your days here, you'll find endless opportunities for adventure, relaxation and fun. Not sure what to do during your trip to Grand Boulevard? Nearby attractions like University of Chicago, Chicago Museum of Science and Industry and Guaranteed Rate Field are good places to start. Whatever your travel plans or the size of your budget, booking your ideal Grand Boulevard vacation is a cinch with Expedia.
The Latest Grand Boulevard Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $592, price is now $357 per person
$357
per person
Feb 20 - Feb 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
All of the above. Staff was wonderful. Room was clean and comfortable. On site amenities were great and food was superb. Best espresso martini I’ve ever tasted.
Reviewed on Dec 11, 2025
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $613, price is now $373 per person
$373
per person
Mar 5 - Mar 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
The rooms were great. Very spacious, fully stocked kitchen and extremely clean. We loved having access to the 8th floor with the steam room, sauna, fitness center, game rooms, and socializing areas 24/7. Would love to experience it in the summer with the pool and outdoor areas. We were also fortunate enough to attend during their Christmas Brunch buffet which was such a great perk! If the price stays around the same, I will continue to stay at Level hotels exclusively in any cities I visit that has one! I’ve already told so many people about my wonderful hotel experience.
Reviewed on Dec 9, 2025
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was $610, price is now $377 per person
$377
per person
Mar 5 - Mar 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Concierge not helpful and neither is was the door man,
Neither would get me a cab, they said to just stand outside
Reviewed on Dec 4, 2025
Where to stay in Grand Boulevard
Find the best Grand Boulevard areas and neighborhoods for the activities you enjoy most. Learn more about Grand Boulevard
Downtown Chicago
5 out of top 10 points of interest in this area
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
Grand Boulevard Hotel Deals
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
$96 nightly
The price is $113 total per night from Jan 6 to Jan 7
$113 total
Jan 6 - Jan 7, 2026
Total with taxes and fees
8.4/10 Very Good! (5,361 reviews)
Everything was prefect. My only gripe was the heat was not heating as it should on 80 degrees. It was 20 degrees outside everyday. Other than that i will definitely return for another stay.. staff and Valetn were very professional and accommodating...10 star stay...
Reviewed on Dec 10, 2025
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
$81 nightly
The price is $95 total per night from Jan 5 to Jan 6
$95 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
8.8/10 Excellent! (3,469 reviews)
Excellent hôtel, right in the center of town,parking valet or self parking available but expensive as expected. Staff was friendly and super attentive, Cafe restaurant right in the hotel. The best is the hotel is at walking distance to everything downtown also bus available up the street on Michigan ...
Reviewed on Dec 12, 2025
Silversmith Hotel Chicago Downtown
10 S Wabash Ave Chicago IL
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $149 total per night from Dec 21 to Dec 22
$149 total
Dec 21 - Dec 22
Total with taxes and fees
9.2/10 Wonderful! (2,109 reviews)
Awesome stay in an amazing room - lobby and bar/restaurant area were excellent as well. Location was perfect for our show at the CIBC Theatre nearby.
Reviewed on Dec 10, 2025
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.
Things to do
Chicago Bulls Basketball Game at United Center
$98
per adult
80% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
$45
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.