Uptown Vacations from $613
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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.
DoubleTree by Hilton Chicago - Alsip
Save 100% on your flight
Price was $957, price is now $613 per person
$613
per person
Sep 12 - Sep 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (1,079 reviews)
Incredible, kind and helpful staff throughout the property..
Reviewed on Jun 18, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,511, price is now $947 per person
$947
per person
Aug 26 - Aug 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,557 reviews)
The hotel and location are beautiful but there needs to be much clearer signage as to where the entrance of the hotel is and the main lobby. Extremely confusing to travellers.
Reviewed on Jun 23, 2026
Hotel Saint Clair- Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $1,219, price is now $787 per person
$787
per person
Aug 26 - Aug 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (1,984 reviews)
Older hotel in River North. Microscopic lobby. Occasionally disinterested desk staff. Immaculate room, great a/c, good shower and good water pressure, comfortable bed, and quiet. "Amenities" weren't exactly visible but, to a fair extent, that reflects the small footprint of the hotel. I'd stay there again.
Reviewed on Jun 23, 2026
Thompson Chicago, by Hyatt
Downtown Chicago
Save 100% on your flight
Price was $2,611, price is now $1,717 per person
$1,717
per person
Sep 12 - Sep 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,399 reviews)
I truly enjoyed my stay at this hotel. From the moment I arrived, the staff made me feel welcome and valued. Everyone was so friendly, attentive, and genuinely eager to help, which made the experience even more enjoyable.
The hotel was clean, comfortable, and had everything I needed for a relaxing stay. I especially loved the location—it was convenient to restaurants, shopping, and local attractions, making it easy to get around and enjoy the area without any hassle.
Reviewed on Jun 21, 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
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.
Uptown Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$128 nightly
The price is $152 total per night from Jun 29 to Jun 30
$152 total
Jun 29 - Jun 30
Total with taxes and fees
8/10 Very Good! (10,177 reviews)
"Great location for see the city. Staff is very friendly and helpful. The only problem we had was the a/c unit was leaking water on the floor the staff came in the room and turned off the a/c unit and left a fan to help with the summer heat. Parking was expensive but very close to the hotel. Parking ..."
Reviewed on Jun 24, 2026
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
$147 nightly
The price is $175 total per night from Jun 30 to Jul 1
$175 total
Jun 30 - Jul 1
Total with taxes and fees
9/10 Wonderful! (4,454 reviews)
"Good location, bar and brunch were great. View from the pool and fitness centers was u real. Room was clean but sink faucet was loose and leaking and the bathroom door locks didn’t work well or would stick. Other than that it was nice."
Reviewed on Jun 24, 2026
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $142 total per night from Jul 2 to Jul 3
$142 total
Jul 2 - Jul 3
Total with taxes and fees
7.8/10 Good! (1,624 reviews)
"Great location! Very close to Magnificent Mile, restaurant's, and the Museum of Ice Cream. The showers are really tight. Other than that the junior suite was perfect for the price and location. I would definitely book again."
Reviewed on Jun 24, 2026
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.
Discover the most popular places to visit in Uptown
Aragon Ballroom
Catch an event at Aragon Ballroom during your trip to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theater scene.
Montrose Beach
Soak up the sun with views of Lincoln Park and Lake Michigan at this city beach known for its fun sports and extensive amenities.
Montrose Harbor
With trails, a beach and a bird sanctuary, this spacious city harbor is a good place to sail from and a great place to hang out.
Things to do
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
88% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.