Near North Side Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to AU$703 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Your Near North Side Holiday

Your next escape beckons with a holiday package to Near North Side. Entertainment, relaxation and nonstop great times — you're sure to find it in this neighbourhood. 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 holiday to Near North Side, Expedia is here to help.

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 featuring a city

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.

Find hotels in Downtown Chicago

Our pick of the best Near North Side Hotel Deals

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
The price is AU$217 per night from 23 Mar to 24 Mar
AU$217
23 Mar - 24 Mar
includes taxes & fees
8.6/10 Excellent! (5,753 reviews)
Good

Reviewed on 16 Mar 2026

Embassy Suites by Hilton Chicago Downtown River North
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$259 per night from 22 Mar to 23 Mar
AU$259
22 Mar - 23 Mar
includes taxes & fees
9.4/10 Exceptional! (3,545 reviews)
The shower pressure is awful and doesn’t get hot

Reviewed on 16 Mar 2026

Hotel Riu Plaza Chicago
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$173 per night from 23 Mar to 24 Mar
AU$173
23 Mar - 24 Mar
includes taxes & fees
9/10 Wonderful! (3,932 reviews)
The view was amazing! The restaurant downstairs was great! It was very hot in our room even with the windows open and the pullout couch was extremely uncomfortable.

Reviewed on 16 Mar 2026

Hilton Chicago/Magnificent Mile Suites
See all 1,064 properties in Near North Side
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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

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.

Discover the most popular places to visit in Near North Side

John Hancock Center featuring a city, night scenes and landscape views

875 North Michigan Avenue

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.

875 North Michigan Avenue
Water Tower Place

Water Tower Place

Enjoy endless shopping, see exhibits of sporting memorabilia and attend shows at a live theater at this huge shopping mall.

Water Tower Place

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.

360 CHICAGO

Activities

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

AU$37
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

AU$57
per adult
92% of travellers recommend
Art Institute of Chicago
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

AU$62
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.