Near North Side Holidays from AU$1,156

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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.

Top Holiday Package Deals in Near North Side

Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was AU$1,671, price is now AU$1,156 per person
AU$1,156
per person
12 Jan - 19 Jan
found 22 hours ago
Return direct flight included
Mexico City (MEX) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
My family and I stayed at The Wit for Thanksgiving and were extremely pleased with the amenities and professionalism of the staff.

Reviewed on 8 Dec 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was AU$3,270, price is now AU$2,044 per person
AU$2,044
per person
12 Jan - 19 Jan
found 22 hours ago
Return direct flight included
Mexico City (MEX) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Amazing hotel, location, staff, and food!!

Reviewed on 8 Dec 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was AU$1,908, price is now AU$1,239 per person
AU$1,239
per person
12 Jan - 19 Jan
found 22 hours ago
Return direct flight included
Mexico City (MEX) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
The room was beautiful and clean and a good city view of the city

Reviewed on 26 Nov 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was AU$1,745, price is now AU$1,185 per person
AU$1,185
per person
12 Jan - 19 Jan
found 22 hours ago
Return direct flight included
Mexico City (MEX) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Wife and I stayed here for 3 nights while visiting family. The Riu is a newer hotel and it shows! The place was modern, clean and well kept. Staff were really nice and helpful. They did an amazing job at the lobby bar and breakfast buffet. I was pleasantly surprised to see that the prices at the bar were on par or cheaper than local cocktail bars -$18 for an Wild Turkey 101 Old Fashioned! The breakfast buffet was a great bonus, we only waited a few minutes to be seated on Sat @10 am. Food was high quality and they provide a lot of options. All in all it was a really nice stay! Would definitely stay at a Riu hotel again and highly recommend to anyone else

Reviewed on 10 Dec 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was AU$1,909, price is now AU$1,319 per person
AU$1,319
per person
12 Jan - 19 Jan
found 22 hours ago
Return direct flight included
Mexico City (MEX) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Concierge not helpful and neither is was the door man, Neither would get me a cab, they said to just stand outside

Reviewed on 4 Dec 2025

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
Fully refundableReserve now, pay when you stay
The price is AU$177 per night from 17 Dec to 18 Dec
AU$177
17 Dec - 18 Dec
includes taxes & fees
8.4/10 Very Good! (5,355 reviews)
Very nice rooms and happy hour!

Reviewed on 6 Dec 2025

Embassy Suites by Hilton Chicago Downtown River North
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$143 per night from 11 Jan to 12 Jan
AU$143
11 Jan - 12 Jan 2026
includes taxes & fees
8.8/10 Excellent! (3,431 reviews)
Great

Reviewed on 4 Dec 2025

Hilton Chicago/Magnificent Mile Suites
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
660 North State Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$153 per night from 11 Jan to 12 Jan
AU$153
11 Jan - 12 Jan 2026
includes taxes & fees
8.8/10 Excellent! (3,145 reviews)
Great location, nearby places for dinning and shopping. Easy access to transportation

Reviewed on 7 Dec 2025

Eurostars Magnificent Mile
See all 1,051 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.
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beach holidays
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Frequently asked questions

How much does a Near North Side holiday package cost?
Starting from only AU$1,156, 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

Water Tower Place

Water Tower Place

4.5/5(16 reviews)

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

Water Tower Place
875 North Michigan Avenue

875 North Michigan Avenue

4.5/5(36 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 acclaimed art galleries.

875 North Michigan Avenue

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 acclaimed art galleries.

360 CHICAGO

Activities

Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

AU$69
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Art Institute of Chicago

Art Institute of Chicago

AU$62
per adult
92% of travellers recommend
Art Institute of Chicago
Lineup with Capone and Dillinger!

Chicago Crime and Mob Bus Tour

AU$76
per adult
90% of travellers recommend
Chicago Crime and Mob Bus Tour
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.