Near North Side Vacations from $526
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 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.
Hotel Riu Plaza Chicago
Downtown Chicago
$1,044
per person
Nov 28 - Dec 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
A wonderful hotel. The hotel is in a great location and very convenient. The breakfast is plentiful and delicious
Reviewed on Sep 23, 2026
Level Chicago Fulton Market
Downtown Chicago
$613
per person
Nov 26 - Dec 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (561 reviews)
I loved the balcony and the great view! The kitchenette was a plus along with the provided utensils and necessary items. The laundry are was not something that I used but I could see how it would be a bonus feature. The area by the bed was a little cramped, but it ended up being comfortable. The staff was extremely friendly and helpful and the check in was seamless. The elevators were especially private and convenient. Overall, the extra $ that I paid for my stay was well worth it!
Reviewed on Sep 21, 2026
Level Chicago – Old Town
Downtown Chicago
$656
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (520 reviews)
Amazing stay. Love the balcony view. Parking was easy and accessible. Will be back!
Reviewed on Sep 19, 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
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.
Magnificent Mile
Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.
The Loop
Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.
River North
Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.
Lincoln Park
Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.
Near North Side Hotel Deals
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
$206 nightly
$245 total
Sep 27 - Sep 28
Total with taxes and fees
8/10 Very Good! (2,305 reviews)
"It started out with someone from the desk, being kind enough to get a luggage cart, for us to load and take things to the room. We were not given information regarding breakfast or the rest of the hotel, nor was there anything in the room. The sink in the bathroom was cracked and leaked on the floor ..."
Reviewed on Sep 23, 2026
Hampton Inn Chicago Downtown/Magnificent Mile
160 E Huron Street Chicago IL
$195 nightly
$231 total
Sep 27 - Sep 28
Total with taxes and fees
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Fully refundableReserve now, pay when you stay
$224 nightly
$266 total
Oct 1 - Oct 2
Total with taxes and fees
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.
Stay near popular Near North Side attractions
Merchandise Mart
8.6/10 (419 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.
Water Tower Place
9.0/10 (1,113 reviews)
Enjoy endless shopping, see exhibits of sporting memorabilia and attend shows at a live theater at this huge shopping mall.
875 North Michigan Avenue
9.2/10 (2,926 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 fascinating museums.
House of Blues Chicago
8.8/10 (159 reviews)
You can get tickets for a performance at House of Blues Chicago during your stay in Chicago. Stroll along the riverfront or experience the acclaimed theater scene in this vibrant area.
Chicago Water Tower
9.0/10 (1,235 reviews)
You can learn about the history of Chicago with a visit to Chicago Water Tower. Amble around this vibrant area's lakeside or experience its acclaimed art scene.
360 CHICAGO
You can learn about the history of Chicago with a visit to 360 CHICAGO. Amble around this vibrant area's riverfront or experience its entertainment choices.
Museum of Contemporary Art Chicago
9.0/10 (88 reviews)
You can spend an afternoon browsing the exhibits at Museum of Contemporary Art Chicago during your travels in Chicago. Stroll along the riverfront or experience the acclaimed theater scene in this vibrant area.
Bally's Casino Chicago
Why not try your luck with a visit to Bally's Casino Chicago during your visit to Chicago? Experience the acclaimed theater scene and entertainment choices in this vibrant area.
Things to do
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
90% of travellers recommend
Explore a world of travel with Expedia
- Hyatt Hotels in Downtown Chicago
- Hilton Hotels in Downtown Chicago
- 5 Star Hotels in River North
- Motels in Chicago
- Free Parking Hotels in Magnificent Mile
- Cabins in Chicago
- Gold Coast Hotels
- Magnificent Mile Hotels
- Downtown Chicago Hotels
- River North Hotels
- Luxury Hotels in Magnificent Mile
- 4 Star Hotels in Magnificent Mile
- Near North Side Hotels
- Flights from Los Angeles (LAX) to Chicago (MDW)
- Delta Air Lines Atlanta (ATL) to Chicago (MDW) flights
- Flights from Atlanta (ATL) to Chicago (MDW)
- Flights to Berwyn
- Porter Airlines Toronto (YTZ) to Chicago (MDW) flights
- Flights to Chicago
- Flights to Rosemont
- Flights to Oak Park
- Flights to Evanston
- Flights to Midway Intl.
- Chicago All Inclusive Vacation Packages
- Chicago Vacations
- Bensenville Vacations
- Where to stay in Oakbrook Terrace
- Visit Downtown Chicago
- Visit West Loop
- Chicago All Inclusive Vacation Packages
- Oak Park Vacations
- Where to stay in Central Chicago
- Chicago All Inclusive Vacation Packages
- Bellwood Vacations
- Rosemont Vacations
- Where to stay in North Pullman
- Central Chicago All Inclusive Vacation Packages
- Schaumburg Vacations
- Visit The Loop
- Chicago Cultural Center
- Central Chicago All Inclusive Vacation Packages
- Chicago All Inclusive Vacation Packages
- Central Chicago All Inclusive Vacation Packages
- Where to stay in Bridgeview
- Central Chicago All Inclusive Vacation Packages
- Visit Chicago
- Chicago Water Tower
- Art Institute of Chicago
- Where to stay in Glenview
- Central Chicago All Inclusive Vacation Packages
- Blue Island Vacations
- Where to stay in South Side
- Visit Gold Coast
- Chicago All Inclusive Vacation Packages
- Visit Lincoln Park
- Visit United Center
- Where to stay in Chicago
- Westchester Vacations
- Chicago Riverwalk
- Where to stay in Oak Park
- Visit Magnificent Mile
- Where to stay in Rosemont
- Visit Rush Street
- Chicago All Inclusive Vacation Packages
- Where to stay in Evanston
- Visit Streeterville
- Darien Vacations
- Visit South Loop
- Where to stay in Cicero
- Downtown Chicago Vacations
- Car rentals near The Loop
- Car rentals near Magnificent Mile
- Hertz Rental Cars in Downtown Chicago
- Car rentals near Downtown Chicago
- SUV Car Rentals in Chicago
- Car rentals near Chicago
- Car rentals near Gold Coast
- Car rentals near River North
- Minivan Car Rentals in Chicago
- Enterprise Rental Cars in Downtown Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.