Near North Side Holidays from AU$3,648

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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.
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
per person
22 Dec - 28 Dec
found 11 hours ago
Return flight included
Sydney (SYD) to Chicago (ORD)
9/10 Wonderful! (809 reviews)
Very cool property. Easy access to shopping and dinning. Amazing room with nice shower and bed.

Reviewed on 10 Nov. 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
22 Dec - 28 Dec
found 11 hours ago
Return flight included
Sydney (SYD) to Chicago (ORD)
9.4/10 Exceptional! (1,390 reviews)
The hotel was beautiful, fabulous location , my only concern that I’m only giving 4 and not 5 is because we were not greeted on arrival, nothing was explained, boarding on rudeness. Bell man great

Reviewed on 9 Nov. 2024

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
22 Dec - 28 Dec
found 11 hours ago
Return flight included
Sydney (SYD) to Chicago (ORD)
9.4/10 Exceptional! (888 reviews)
The staff were all wonderful and really helpful. It was our first time in Chicago and they were more than wonderful for pointing us in the correct locations on where we needed to go and what to do

Reviewed on 5 Nov. 2024

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
per person
22 Dec - 28 Dec
found 11 hours ago
Return flight included
Sydney (SYD) to Chicago (ORD)
9.8/10 Exceptional! (1,001 reviews)
The service at the Langham is impeccable.

Reviewed on 4 Nov. 2024

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
per person
22 Dec - 28 Dec
found 11 hours ago
Return flight included
Sydney (SYD) to Chicago (ORD)
9.2/10 Wonderful! (2,021 reviews)
We enjoyed the rooms!! Beautiful view of the city and lake!! The sunrise and sunset view is amazing.

Reviewed on 10 Nov. 2024

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

Known for its fascinating museums, stunning river views and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Michigan Avenue and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotel + flight trips 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$211 per night from 24 Nov to 25 Nov
AU$211
includes taxes & fees
24 Nov - 25 Nov
8.2/10 Very Good! (3,184 reviews)
"Very clean!"

Reviewed on 10 Nov. 2024

Embassy Suites by Hilton Chicago Downtown River North
The Westin Michigan Avenue Chicago
The Westin Michigan Avenue Chicago
4.5 out of 5
909 North Michigan Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$277 per night from 25 Nov to 26 Nov
AU$277
includes taxes & fees
25 Nov - 26 Nov
8.6/10 Excellent! (1,006 reviews)
"It’s such a classic Westin property, in the heart of the city!!"

Reviewed on 9 Nov. 2024

The Westin Michigan Avenue Chicago
Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel
Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel
3.5 out of 5
350 West Wolf Point Plaza, Building 2, Chicago, IL
Fully refundable
The price is AU$192 per night from 26 Nov to 27 Nov
AU$192
includes taxes & fees
26 Nov - 27 Nov
8.6/10 Excellent! (1,175 reviews)
"I made a last minute reservation since I was bumped off a late night Southwest Airline to Philadelphia and the accomodations were magnificent"

Reviewed on 6 Nov. 2024

Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel
See all 1,025 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 AU$3,648, 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

Image for Navy Pier

Navy Pier

4.5/5(64 reviews)

A waterfront entertainment strip with fun diversions for both young and old, with shops, restaurants and even a Ferris wheel.

Navy Pier
Image for 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
Image for Oak Street Beach

Oak Street Beach

Why not spend a care-free afternoon at Oak Street Beach during your travels in Chicago? Stroll along the riverfront or experience the acclaimed theatre scene in this vibrant area.

Oak Street Beach

Activities

Image for Flyover in Chicago

Flyover in Chicago

AU$58
Per adult
94% of travellers recommend
Flyover in Chicago
Image for Chicago River Cocktail Cruise

Chicago River Cocktail Cruise

AU$90
Per adult
90% of travellers recommend
Chicago River Cocktail Cruise
Image for Chicago River Architecture Tour with Small Boat Upgrade Option

Chicago River Architecture Tour with Small Boat Upgrade Option

AU$74
Per adult
98% of travellers recommend
Chicago River Architecture Tour with Small Boat Upgrade Option
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.