Near North Side Vacation Packages
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Top Holiday Package Deals in Near North Side
Price found within the past 48 hours. Click for updated prices.
Freehand Chicago
Downtown Chicago
CA $1,759
per person
Oct 8 - Oct 12
found 6 hours ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
7.8/10 Good! (3,367 reviews)
Clean, freindly Staff, good location- the+'s.
Should of known to bring towels and parking was kidde korner from entrance not next to it. 4.75 stars
Reviewed on Sep 4, 2026
The Talbott, Autograph Collection
Downtown Chicago
CA $1,153
per person
Oct 21 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (159 reviews)
The room was spacious for two. The location was easy to reach from the bus line. We were able to check in early! The only problems were that the phone would ring randomly throughout the morning. We didn't ask for any wake-up calls, and you could hear through the walls into the next room. All in all, the hotel location was a good choice for this trip.
Reviewed on Sep 2, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
CA $1,195
per person
Oct 21 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (2,685 reviews)
My family (of 4) stayed 5 days/4 nights. The room had a beautiful view. The room itself was very nice too! Front desk staff were nice and helpful. The only thing we didn't like was the housekeeping. We requested more towels because only 3 towels were in the bathroom, and we needed one more. It took a long time for it to be sent to our room. We had to request 4 towels every time, which was annoying. Also, there were 2 days our room was not cleaned, even after we requested housekeeping. Other than that, the hotel itself was great. We ate at the restaurant downstairs for breakfast and dinner on occasion. The surrounding area was beautiful and picturesque. We would stay at Sable Hotel again!
Reviewed on Sep 3, 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.
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.
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.
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
CA $179
CA $213 total
Sep 30 - Oct 1
includes taxes & fees
8/10 Very good! (2,152 reviews)
"I enjoyed this room truly! the place was perfectly located! loved the stay and will for sureee book again"
Reviewed on Sep 4, 2026
Hampton Inn Chicago Downtown/Magnificent Mile
160 E Huron Street Chicago IL
CA $192
CA $229 total
Sep 7 - Sep 8
includes taxes & fees
8/10 Very good! (1,566 reviews)
"Parking : called ahead to ask about parking our trailer we pulled and was told a garage to use then it was an issue once we got there."
Reviewed on Sep 3, 2026
Kasa Magnificent Mile Chicago
One Superior Place Chicago IL
9.4/10 Exceptional! (888 reviews)
"We thoroughly enjoyed our stay at Kasa- check in instructions were clear and hassle free. The unit was spacious and clean, with a terrific view. Highly recommended!"
Reviewed on Sep 4, 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.
Frequently asked questions
How much does a Near North Side vacation package cost?
Starting from only CA $1,114, a package is your passport to low-cost travel. Put together your Near North Side trip by picking from our wide range of hotels, airfares and rental cars.
How do I get a cheap travel package to Near North Side?
Secure flights that fit in with your schedule, add a hotel to your booking and watch the savings rack up with a Near North Side vacation package. It's that simple! From hotels and flights to rental cars and tours, Expedia makes traveling cheaply a cinch. And with more than 550 partner airlines and 1,000,000 properties throughout the world to choose from, you'll never be short of choice.
Where should I stay in Near North Side?
Vacationers come from all over to see McCormick Place and Millennium Park in Near North Side. Book a room near these awesome attractions and visit them whenever you please.
What are the top hotels in Near North Side?
Sable at Navy Pier Chicago, Curio Collection by Hilton and Kasa River North Chicago are a couple of the most well-known properties in Near North Side. Why not take a look at the facilities and rates at each and then decide?
How far in advance should I book my Near North Side vacation?
Travelers can normally compare international flights on Expedia within 12 months of departure. Booking late? With a stroke of luck, it's still possible to score a cheaper ticket only weeks before your journey.
What does an Expedia Near North Side travel package include?
Travel packages include hotels, rental cars and flights, but you can mix and match them to create your perfect Near North Side vacation. You can also add on a few activities and tours once you've made your booking. You're in control! When you combine your bookings with Expedia, you'll score deals you won't find elsewhere.
What should I know before booking a Near North Side travel package?
Whether it's relaxation or adventure you're seeking, a Near North Side vacation package lets you organize your escape your way. Plus, you'll get access to great discounts when you combine your accommodations with your flights and rental car. The more you bundle, the bigger the savings!
Can I choose my airline with a Near North Side Expedia vacation package?
Expedia offers access to more than 550 airline partners worldwide, so you sure can! Simply pick the carrier you want and create your ideal Near North Side vacation.
If I'm not able to travel, can I cancel my Near North Side vacation package?
Yes, you can. We get that even the best-laid plans can go awry, so we're here to help if you need to make changes to your Near North Side vacation package. You may be able to cancel or amend your itinerary for free if you've booked in the last 24 hours. Your airline, hotel or car rental company may charge you a fee if you booked more than 24 hours ago. Have a look at our Customer Service Portal for more information. Also, be sure to check your itinerary for the nitty-gritty on change fees.
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 fascinating museums 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.
Photo by daniel jersey
Chicago Children's Museum
9.2/10 (237 reviews)
You can take time to visit Chicago Children's Museum during your travels to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed art scene.
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.
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 fascinating museums.
Things to do
Wendella's Lake and River Architecture Tour
CA $62
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
CA $56
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.