Uptown Vacations from $310
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Your Uptown Vacation
Take the stress out of travel planning with an Uptown vacation package. With all the details organized before you set off, all you have to do is simply enjoy this residential neighborhood's cafes, history and culture. Not sure what to see and do during your trip to Uptown? Nearby attractions like Lincoln Park, Loyola University Chicago and Aragon Ballroom are great places to start. Expedia can help you turn your ideal Uptown vacation into reality, no matter your travel plans or budget.
The Latest Uptown Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Saint Clair- Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $503, price is now $311 per person
$311
per person
Jan 13 - Jan 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (2,334 reviews)
Website VERY misleading, like a “bait and switch “. NO CRAFT COFFEE BAR, finess room is really just a cardio room, superior bedroom decor very dated, only one solo chair for two people (for desk and rolls backwards across the the room so you need to be careful if you are sitting in it and bending down to remove your shoes), absolutely no space to put any toiletries in bathroom, no instructions on TV stations available, no helpful information @ restaurants nearby, funky coffee maker with no operating instructions, king size bed and a whole two hangers for two people, and way more than the advertised price so overpriced! Location great if you don’t mind ambulance sirens (it’s two blocks from Northwest Memorial Hospital).
Reviewed on Oct 30, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $625, price is now $388 per person
$388
per person
Jan 13 - Jan 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (5,555 reviews)
Breakfast buffet was amazing. Would definitely stay here again.
Reviewed on Oct 30, 2026
Where to stay in Uptown
Find the best Uptown areas and neighborhoods for the activities you enjoy most. Learn more about Uptown
Downtown Chicago
4 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.
Uptown Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$104 nightly
The price is $124 total per night from Nov 10 to Nov 11
$124 total
Nov 10 - Nov 11
Total with taxes and fees
8/10 Very Good! (10,064 reviews)
"Good"
Reviewed on Oct 30, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
$134 nightly
The price is $159 total per night from Nov 19 to Nov 20
$159 total
Nov 19 - Nov 20
Total with taxes and fees
8/10 Very Good! (2,624 reviews)
"I was charged $24.00 for a glass of Gin and tonic...carpet in my room was flooded with water...mattress was horrible ... will never return.."
Reviewed on Oct 30, 2026
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
$107 nightly
The price is $127 total per night from Nov 1 to Nov 2
$127 total
Nov 1 - Nov 2
Total with taxes and fees
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.
Stay near popular Uptown attractions
Things to do
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travellers recommend
Chicago's Navy Pier Centennial Wheel Ticket
$24
per adult
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.