Near North Side Holidays from AU$1,798

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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 Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Price was AU$2,837, price is now AU$1,798 per person
AU$1,798
per person
13 Nov - 20 Nov
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9/10 Wonderful! (1,992 reviews)
Our experience here was fantastic. We visited in August and the weather was superb. Everything was centralized. From shopping to dining and peace and quiet were abound. Just magnificent stay. The staff was friendly and informative. Thank you.

Reviewed on 4 Sep. 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$5,090, price is now AU$3,162 per person
AU$3,162
per person
13 Nov - 20 Nov
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.4/10 Exceptional! (1,714 reviews)
Professional service

Reviewed on 4 Sep. 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was AU$3,969, price is now AU$2,500 per person
AU$2,500
per person
13 Nov - 20 Nov
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.2/10 Wonderful! (1,195 reviews)
I loved the location - it was very walkable and lots of restaurants/shops nearby. The room itself was average - beds were very low and the furniture was kind of odd - mostly plywood built ins. But the one room served it's purpose and was clean. The issue was, I had reserved TWO rooms, but when I arrived I was informed they only had one room for me. Apparently they didn't accept the second room reservation... Neither the Emily nor Expedia notified me that one of my "PREPAID" rooms was not reserved. There were NO rooms available in the Hotel for Saturday, nor in the entire city of Chicago on Labor Day weekend, so we were left scrambling to find a place to accomodate the six of us (i.e friends couches, etc.). Not sure which company is ultimately to blame, but needless to say, ALWAYS double check your reservation with this place before you travel.

Reviewed on 3 Sep. 2025

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was AU$5,842, price is now AU$3,970 per person
AU$3,970
per person
13 Nov - 20 Nov
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.8/10 Exceptional! (1,005 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.

Reviewed on 12 Aug. 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was AU$3,388, price is now AU$2,328 per person
AU$2,328
per person
13 Nov - 20 Nov
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.4/10 Exceptional! (1,070 reviews)
Great place esp last minute

Reviewed on 5 Sep. 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
The price is AU$320 per night from 14 Sept to 15 Sept
AU$320
14 Sept - 15 Sept
includes taxes & fees
Embassy Suites by Hilton Chicago Downtown River North
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$299 per night from 22 Sept to 23 Sept
AU$299
22 Sept - 23 Sept
includes taxes & fees
The Wade
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$292 per night from 14 Sept to 15 Sept
AU$292
14 Sept - 15 Sept
includes taxes & fees
Hilton Garden Inn Chicago Downtown/Magnificent Mile
See all 1,062 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$1,798, 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

Navy Pier

Navy Pier

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

Navy Pier
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
John Hancock Center

John Hancock Center

You can find out about the history of Chicago when you stop by John Hancock Center. Amble around this vibrant area's lakeside or experience its acclaimed theatre scene.

John Hancock Center

Activities

River tour boat in Chicago

Architecture River Tour

AU$75
per adult
96% of travellers recommend
Architecture River Tour
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
Chicago: Architecture Boat Tour with Drinks

Chicago: Architecture Boat Tour with Drinks

AU$64
per adult
88% of travellers recommend
Chicago: Architecture Boat Tour with Drinks
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.