Near North Side Vacations from $254
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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.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $418, price is now $254 per person
$254
per person
Feb 13 - Feb 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Great breakfast, Clean room, enjoyed the stay
Reviewed on Jan 9, 2026
Ohio House Motel
Downtown Chicago
Save 100% on your flight
Price was $477, price is now $315 per person
$315
per person
Apr 2 - Apr 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,022 reviews)
Exactly as advertised, cute place, great location.
Reviewed on Jan 5, 2026
Holiday Inn Club Vacations at Lake Geneva Resort by IHG
Save 100% on your flight
Price was $515, price is now $351 per person
$351
per person
Feb 13 - Feb 16
found 6 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
8.8/10 Excellent! (1,003 reviews)
Be warned even though the main pic for this stay shows a waterpark, it is not included with this stay. The room was very nice and the hotel staff was lovely but our grandkids were very disappointed and we had to pay $30 per person/per day for a small waterpark that was is a separate location.
Reviewed on Jan 6, 2026
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 18 to Jan 19
$105 total
Jan 18 - Jan 19
Total with taxes and fees
8.8/10 Excellent! (3,677 reviews)
Room and hotel overall very clean. Noted some things that could be updated in bathroom(stopper in sink didnt go all the way down, peeling caulk and some missing grout). Minor updates. Our sink was clogged when we checked in and I called the front desk, housekeeping and the hotel hotline 4 different ...
Reviewed on Jan 7, 2026
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $110 total per night from Jan 19 to Jan 20
$110 total
Jan 19 - Jan 20
Total with taxes and fees
8.4/10 Very Good! (5,522 reviews)
Had a great stay.
Reviewed on Jan 8, 2026
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 Feb 8 to Feb 9
$101 total
Feb 8 - Feb 9
Total with taxes and fees
8.8/10 Excellent! (3,169 reviews)
Staff was very curious and the room was clean and stunning with the panoramic view. We had a wonderful time.
Reviewed on Jan 9, 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 Near North Side
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.
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 acclaimed theater scene.
Things to do
Skydeck - Willis Tower Admission
$44
per adult
100% of travellers recommend
Chicago Bulls Basketball Game at United Center
$83
per adult
80% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
88% of travellers recommend
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- 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.