Near North Side Vacations from $367
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $1,045 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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 $589, price is now $367 per person
$367
per person
Mar 18 - Mar 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
lovely hotel with wonderful friendly staff, and the perfect location. The beds are lovely and comfortable and the hotel very pretty. However, they need to upgrade the quality of the food preparation. The offerings were very good but the actual preparation of the food was not in line with any of the other Pendry hotels we have stayed in.
Reviewed on Dec 24, 2025
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $657, price is now $386 per person
$386
per person
Mar 4 - Mar 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
The cleanliness of the rooms was great and the breakfast buffet was second to none! Location, location, location….. was the best! One block away from the Magnificent Mile, restaurants, and can I say Trader Joe’s? We will definitely come back.
Reviewed on Dec 25, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $990, price is now $589 per person
$589
per person
Mar 18 - Mar 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Loved it here and would stay again! Everything was perfect!
Reviewed on Dec 21, 2025
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $630, price is now $387 per person
$387
per person
Mar 18 - Mar 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Staff was friendly did amazing job with checking us in
Reviewed on Dec 25, 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
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.
Near North Side Hotel Deals
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $105 total per night from Jan 5 to Jan 6
$105 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
8.8/10 Excellent! (3,549 reviews)
Room was warm Recommend softer toilet paper please
Reviewed on Dec 23, 2025
Eurostars Magnificent Mile
660 North State Street Chicago IL
Fully refundableReserve now, pay when you stay
$86 nightly
The price is $101 total per night from Jan 25 to Jan 26
$101 total
Jan 25 - Jan 26, 2026
Total with taxes and fees
8.8/10 Excellent! (3,152 reviews)
Good
Reviewed on Dec 23, 2025
Warwick Allerton - Chicago
701 North Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$87 nightly
The price is $102 total per night from Jan 25 to Jan 26
$102 total
Jan 25 - Jan 26, 2026
Total with taxes and fees
8.4/10 Very Good! (3,004 reviews)
Clean room
Reviewed on Dec 24, 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
4.5/5(834 reviews)
Enjoy endless shopping, see exhibits of sporting memorabilia and attend shows at a live theater at this huge shopping mall.
Merchandise Mart
4.5/5(333 reviews)
You can learn about the history of Chicago with a trip to Merchandise Mart. Amble around this vibrant area's riverfront or experience its fascinating museums.
875 North Michigan Avenue
4.5/5(1,913 reviews)
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 acclaimed art scene.
Things to do
Chicago Bulls Basketball Game at United Center
$80
per adult
80% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% 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.