Near North Side Vacations from $209
Book a Hotel + Flight or Car together to unlock savings
Your Near North Side Vacation
Your next escape beckons with a vacation package to Near North Side. Entertainment, relaxation and nonstop great times — you're sure to find it in this neighborhood. When it's time to get out and explore, you'll find a lot of popular attractions nearby including Millennium Park, Willis Tower and Art Institute of Chicago. Visit one, two or all during your trip to Near North Side. Stop dreaming and start doing. When you're ready to lock in your vacation to Near North Side, Expedia is here to help.
The Latest Near North Side Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was $346, price is now $209 per person
$209
per person
Jan 23 - Jan 25
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
18.8/10 Exceptional! (1,128 reviews)
A great location, a fabulous building, and a delightful room. The one mystery was a background thumping noise that persisted throughout the stay. Fortunately, didn't disturb sleep. The reception staff sloughed off any knowledge or interest in the cause, but we couldn't imagine that the source was an unknown to hotel staff, and potentially fixable.
Reviewed on Nov 12, 2025
Sand Hill On The Lake
Price was $500, price is now $284 per person
$284
per person
Dec 31 - Jan 3
found 23 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
8.8/10 Excellent! (77 reviews)
The view on the lake is beautiful and the fireplace made it so cozy during our fall visitl
Reviewed on Nov 10, 2025
Hilton Orrington / Evanston
Downtown Evanston
Save 100% on your flight
Price was $959, price is now $574 per person
$574
per person
Dec 27 - Jan 3
found 15 hours ago
Roundtrip flight included
Miami (MIA) to Chicago (ORD)
7.6/10 Good! (1,003 reviews)
Nice staff and easy access to the Northwestern campus.
Reviewed on Nov 13, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $601, price is now $367 per person
$367
per person
Jan 23 - Jan 25
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
18.8/10 Exceptional! (1,773 reviews)
It was absolutely wonderful. We were upgraded to a suite which was pretty sweet (no pun intended)! At night the surrounding view of the lake along the lakeside of the hotel was spectacular. The Rebar on the mezzanine floor with a live musician playing a saxophone on a Saturday, was a cozy and lively setting. Welcome champagne upon check in was a nice touch. The Terrace 16 restaurant/bar also served scrumptious choices on the menu. Overall, very satisfied with our stay.
Reviewed on Nov 14, 2025
Where to stay in Near North Side
Find the best Near North Side areas and neighborhoods for the activities you enjoy most. Learn more about Near North Side
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.
Near North Side Hotel Deals
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
$95 nightly
The price is $112 total per night from Nov 25 to Nov 26
$112 total
Nov 25 - Nov 26
Total with taxes and fees
8.4/10 Very Good! (5,235 reviews)
Clean room; kind and courteous staff; excellent breakfast and happy hour included
Reviewed on Nov 10, 2025
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $115 total per night from Dec 7 to Dec 8
$115 total
Dec 7 - Dec 8
Total with taxes and fees
8.8/10 Excellent! (3,285 reviews)
I loved that everything was in walking distance. It was very clean. The hospitality service was excellent! Very kind and friendly!
Reviewed on Nov 14, 2025
Warwick Allerton - Chicago
701 North Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $104 total per night from Nov 23 to Nov 24
$104 total
Nov 23 - Nov 24
Total with taxes and fees
8.4/10 Very Good! (2,955 reviews)
Wi-fi was HORRIBLE! Even when I paid the $21 extra for extra speed and bandwith.
Reviewed on Nov 8, 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.
Discover the most popular places to visit in Near North Side
Water Tower Place
Enjoy endless shopping, see exhibits of sporting memorabilia and attend shows at a live theater at this huge shopping mall.
875 North Michigan Avenue
You can find out about the history of Chicago with a visit to 875 North Michigan Avenue. Amble around this vibrant area's lakeside or experience its fascinating museums.
Merchandise Mart
You can learn about the history of Chicago with a trip to Merchandise Mart. Amble around this vibrant area's riverfront or experience its acclaimed art scene.
Things to do
Skydeck - Willis Tower Admission
$44
per adult
98% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
84% of travellers recommend
Explore a world of travel with Expedia
- Chicago Hotels
- Hotels near Downtown Chicago
- Cheap Hotels in Chicago
- Hotels near Magnificent Mile
- Hotels near Chicago Riverwalk
- Hotels with Free Airport Shuttle in Chicago
- Hotels near River North
- Cheap Hotels in Downtown Chicago
- Hotels near Michigan Avenue
- Hotels with Free Parking in Chicago
- Luxury Hotels in Downtown Chicago
- Extended Stay Hotels in Chicago
- Hotels near Annunciation Greek Orthodox Cathedral
- Hotels near Dave & Buster's
- Hotels near Newberry Library
- Hotels near Washington Square
- Hotels near The Loop
- Hotels near Clark-Division Station
- Central Chicago Hotels
- Hotels near Rush and Division
- Hotels near Chicago Station
- Rush Street Hotels
- Hotels with a View in Downtown Chicago
- Luxury Hotels in Magnificent Mile
- Hotels near Navy Pier
- Hotels near Gold Coast
- Hotels near ArchiTech Gallery
- Hotels near Chicago Station
- Luxury Hotels in Rush Street
- Boutique Hotels in Rush Street
- Historic Hotels in Rush Street
- Pet-friendly Hotels in Rush Street
- 5 Star Hotels in Rush Street
- Hotels with Air Conditioning in Rush Street
- Hotel Wedding Venues Hotels in Rush Street
- Beach Hotels in Rush Street
- Resorts & Hotels with Spas in Rush Street
- Motels in Rush Street
- Golf Hotels in Rush Street
- Guest Houses in Rush Street
- Hotels near Oak Street
- Hotels near Millennium Park
- Hotels near Aldo Castillo Gallery
- Hotels near Grant Park
- Hotels with Free Parking in Magnificent Mile
- Hotels near Holy Name Cathedral
- Chicago Vacations
- Visit Downtown Chicago
- Dave & Buster's
- Annunciation Greek Orthodox Cathedral
- Newberry Library
- John Hancock Center
- Cooking & Hospitality Institute of Chicago
- Water Tower Place
- Holy Name Cathedral
- Rush Street Vacations
- Chicago Water Tower
- Navy Pier
- Aldo Castillo Gallery
- 900 North Michigan Shops
- Fourth Presbyterian Church
- Oak Street Beach
- Lookingglass Theatre
- Chinese Consulate
- Chicago Place Mall
- St. James Cathedral
- Magnificent Mile Vacations
- Driehaus Museum
- Broadway Playhouse
- River North Vacations
- Chicago History Museum
- Ann and Robert H. Lurie Children's Hospital
- Gold Coast Vacations
- Shops at North Bridge
- Northwestern Memorial Hospital
- Visit Rush Street
- American Medical Association Headquarters
- Cyrus McCormick Mansion
- Michigan Avenue
- Prentice Women's Hospital
- The East Bank Club
- Tribune Tower
- Streeterville Vacations
- Ohio Street Beach
- International Museum of Surgical Science
- Chicago Riverwalk
- Ronald McDonald House near Lurie Children’s
- Chicago Theatre
- Wrigley Building
- Richard Norton Gallery
- Museum of Broadcast Communications
- Marina City
- Merchandise Mart
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.