Near North Side Vacations from $436
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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.
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $866, price is now $522 per person
$522
per person
Mar 17 - Mar 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
I stayed 5 nights total, 4 nights in a two BR, 1 bath with a balcony and the last night in a one BR. The 2BR was great. It faced East, received a lot of sunlight, was clean, modern and the bed was very comfortable. The gym had what I needed too. actually liked sleeping with the sound of the el nearby because I used to live in the area. I did not give it 5 stars because the walls are super thin. Someone had a party next to me and it was impossible to sleep hearing voices straight through the walls. Being a newer building, I don’t think the best quality appliances or fixtures were chosen. My ice machine wasn’t working and the heat/fan only worked in certain areas in the 2BR. Additional lighting should be added. The 1BR shower fixtures and drain needed some attention. That said, Mihajlo and the front desk staff were very helpful and attentive and helped me with whatever I needed. The 1BR seemed more like a studio to m. I’d prefer to book directly through Level, but it was a better price with Expedia. I still thought it was pricey but I was overall happy with my stay.
Reviewed on Jan 12, 2026
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $984, price is now $596 per person
$596
per person
Mar 17 - Mar 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
Had an amazing stay. Just note, you need to ask for the room cleaning service, and its not for everyday. Overall really loved the place and hope to come back!
Reviewed on Jan 10, 2026
The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was $859, price is now $525 per person
$525
per person
Mar 17 - Mar 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
room was clean, comfortable, & staff were kind and welcoming
Reviewed on Jan 12, 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
$80 nightly
The price is $94 total per night from Feb 1 to Feb 2
$94 total
Feb 1 - Feb 2
Total with taxes and fees
8.8/10 Excellent! (3,706 reviews)
10/10
Reviewed on Jan 14, 2026
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
$107 nightly
The price is $126 total per night from Jan 19 to Jan 20
$126 total
Jan 19 - Jan 20
Total with taxes and fees
8.4/10 Very Good! (5,539 reviews)
The room was clean. The staff was friendly. The breakfast was not great, but not bad.
Reviewed on Jan 14, 2026
Holiday Inn Chicago Dwtn - The Mart by IHG
350 West Wolf Point Plaza, Building 2 Chicago IL
Fully refundable
$110 nightly
The price is $129 total per night from Jan 18 to Jan 19
$129 total
Jan 18 - Jan 19
Total with taxes and fees
8.8/10 Excellent! (2,112 reviews)
Clean room, great location downtown, great amenities.
Reviewed on Jan 14, 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.