Near North Side Holidays
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Our guide on 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
Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.
Magnificent Mile
An avenue brimming with superb shops and restaurants, the Magnificent Mile more than lives up to its name.
River North
Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.
Theatre District
While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more of the city at Washington Station or Monroe Station (Blue Line).
Our pick of the best 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
NZ$289
30 Aug - 31 Aug
includes taxes & fees
8/10 Very good! (1,981 reviews)
"There was mold on the curtains."
Reviewed on 11 Aug 2026
Holiday Inn Chicago Dwtn - The Mart by IHG
350 West Wolf Point Plaza, Building 2 Chicago IL
Fully refundable
NZ$461
7 Sept - 8 Sept
includes taxes & fees
8.8/10 Excellent! (2,507 reviews)
"The rooms didn't have a microwave in there."
Reviewed on 10 Aug 2026
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Fully refundableReserve now, pay when you stay
NZ$260
31 Aug - 1 Sept
includes taxes & fees
7.8/10 Good! (1,931 reviews)
"Had to pay a premium just to use amenities. Stood in a long line to check out for 20 min. Barely any staff."
Reviewed on 11 Aug 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 holiday package cost?
Starting from only , 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 holiday package. It's that simple! From hotels and flights to rental cars and tours, Expedia makes travelling 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?
Holiday Makers 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 holiday?
Travellers 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 holiday. 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 holiday package lets you organise your escape your way. Plus, you'll get access to great discounts when you combine your accommodation 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 holiday 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 holiday.
If I'm not able to travel, can I cancel my Near North Side holiday 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 holiday 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
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 when you stop by 875 North Michigan Avenue. Amble around this vibrant area's lakeside or experience its fascinating museums.
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.
House of Blues Chicago
8.8/10 (159 reviews)
You can get tickets for a performance at House of Blues Chicago during your trip to Chicago. Stroll along the riverfront or experience the fascinating museums in this vibrant area.
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 galleries.
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 galleries.
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.
Museum of Contemporary Art Chicago
9.0/10 (88 reviews)
You can spend an afternoon studying the exhibits at Museum of Contemporary Art Chicago during your trip to Chicago. Stroll along the riverfront or experience the acclaimed theatre scene in this vibrant area.
Activities
Chicago: Navy Pier Centennial Wheel Ticket
NZ$42
per adult
90% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.