North Side Holidays from AU$2,271

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The Latest North Side Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Chicago Marriott Suites Deerfield

Chicago Marriott Suites Deerfield

4 out of 5
Price was AU$2,360, price is now AU$2,271 per person
AU$2,271
per person
6 Aug - 8 Aug
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
8.6/10 Excellent! (1,000 reviews)
The staff was very helpful

Reviewed on 8 June 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was AU$3,040, price is now AU$2,814 per person
AU$2,814
per person
6 Aug - 8 Aug
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.2/10 Wonderful! (491 reviews)
Room was not cleaned/ towels weren't replaced for the duration of our 3 night stay which I found rather peculiar. They also only provided 1 key for our room. I had believed it was common practice to provide 2. Other than that, the room was clean when we arrived, the bedding was comfortable, and the gym was lovely.

Reviewed on 22 May 2026

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Price was AU$2,620, price is now AU$2,461 per person
AU$2,461
per person
6 Aug - 8 Aug
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
8.4/10 Very Good! (2,308 reviews)
I needed help with my luggage to United and Mike a bellman as extremely helpful.

Reviewed on 7 June 2026

Nobu Hotel Chicago

Nobu Hotel Chicago

5 out of 5
Downtown Chicago
Price was AU$3,180, price is now AU$2,990 per person
AU$2,990
per person
6 Aug - 8 Aug
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.4/10 Exceptional! (860 reviews)
Beautiful room. Well appointed. love the ambiance. Ashley Cartagena was very helpful with reservations!! Great location. Do not eat here, food is not good especially for the price. Rooftop bar view is cute but cocktails not great, I would skip them. There are dozens of cute coffee shops, bakeries, restaurants, bars & shops all steps away. would definitely stay here again.

Reviewed on 28 May 2026

Staybridge Suites Chicago O'Hare - Rosemont by IHG

Staybridge Suites Chicago O'Hare - Rosemont by IHG

3 out of 5
Price was AU$2,743, price is now AU$2,640 per person
AU$2,640
per person
6 Aug - 8 Aug
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.2/10 Wonderful! (1,185 reviews)
Outstanding Hotel and close to car rental drop off and straight to your terminal. 3rd time staying at hotel, my favorite. 💯

Reviewed on 3 June 2026

Our guide on where to stay in North Side

Find the best North Side areas and neighborhoods for the activities you enjoy most. Learn more about North Side
Lincoln Park

Lincoln Park

7 out of top 10 points of interest in this area
5/5(4 area reviews)

Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.

Find hotels in Lincoln Park

North Side Holiday

North Side Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Top Sights
Lincoln Park Zoo, North Avenue Beach and Lincoln Park

Our pick of the best North Side Hotel Deals

The Majestic Hotel

The Majestic Hotel

3 out of 5
528 W Brompton Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$283 per night from 6 July to 7 July
AU$283
6 July - 7 July
includes taxes & fees
8.8/10 Excellent! (1,014 reviews)
"Awesome"

Reviewed on 7 June 2026

The Majestic Hotel
Hotel Lincoln

Hotel Lincoln

4 out of 5
1816 N Clark Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$262 per night from 1 July to 2 July
AU$262
1 July - 2 July
includes taxes & fees
7.8/10 Good! (1,133 reviews)
"Chipped finishes in the bathtub/shower. TV didn't work. Safe didn't work. Threadbare towels. Leak from another room in our bathroom. All of the above reported to front desk, but attitude poor, nothing fixed and no discount or other consideration offered. Happy to check out and go to a different hotel ..."

Reviewed on 8 June 2026

Hotel Lincoln
The Willows Hotel

The Willows Hotel

3 out of 5
555 W Surf St Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$228 per night from 8 July to 9 July
AU$228
8 July - 9 July
includes taxes & fees
8.6/10 Excellent! (1,012 reviews)
"Love this property - great location, and very nice & helpful staff."

Reviewed on 7 June 2026

The Willows Hotel
See all 564 properties in 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
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All Inclusive Holidays
Cheap Holidays
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Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Discover the most popular places to visit in North Side

Lincoln Park Zoo

Lincoln Park Zoo

4.5/5(7 reviews)

This small zoo right in the heart of Chicago, Lincoln Park is an ideal family destination, popular with small children eager to see the many different animals.

Lincoln Park Zoo
Lincoln Park Conservatory

Lincoln Park Conservatory

This glass structure full of exotic plants is the perfect place to spend a quiet afternoon.

Lincoln Park Conservatory

Lincoln Hall

You can get tickets for a performance at Lincoln Hall during your stay in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theatre scene.

Lincoln Hall

What to do in North Side

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

AU$34
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

AU$64
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
Art Institute of Chicago

Art Institute of Chicago

AU$56
per adult
92% of travellers recommend
Art Institute of Chicago
See all activities in North Side

Frequently asked questions

Can I cancel my flight booking to North Side due to COVID-19?
In these difficult times, many carriers are offering more flexibility. Head to our Customer Service Portal for details about cancelling or amending your flight due to COVID-19.
What's the best way to find cheap flights to North Side that have flexible change policies?
We understand that travel schedules can change in the blink of an eye, so choosing a flexible fare with Expedia is a wise idea. Simply mark the "No change fee" box directly below the "Flexible change policies" filter. Your low-cost, flexible flight to North Side is only a few clicks away.
What are some of the general tips for travellers to North Side during the COVID-19 outbreak?
With new COVID-19 safety measures to follow, travel looks a bit different in this day and age. Here are a few things to know before you hop on that plane to North Side:
  • Investigate if any restrictions apply to both your origin and destination. You may not be able to travel depending on local circumstances, so don't forget to check government advisories before booking.
  • When you go through airport screening, keep your face mask on. You will be asked to lower it briefly for ID purposes. Anyone refusing to wear a mask may be denied entry or boarding.
  • Rather than handing a TSA agent your boarding pass, position it directly on the scanner yourself. After that, hold it up for inspection.
  • You are now permitted to take one container of hand sanitizer up to 12 oz (350 ml) in your carry-on baggage. You'll need to remove it for X-ray screening.
  • Remove personal items from your pockets, like your phone, keys and wallet, and put them in your carry-on instead of into bins. This will minimize handling during screening.
  • Separate any food you have for X-ray screening. Food items often trigger the alarm. Putting them in a clear plastic bag and into a bin reduces the need for a TSA employee to touch and inspect your belongings.

Which airlines fly to North Side?
Let American Airlines take you there. This popular carrier provides 13307 flights a month to O'Hare Intl. Airport (ORD), a North Side gateway.
How can I find cheap tickets to North Side?
An effective strategy for nabbing cheap airfares is to be flexible with your dates. Begin with searching for your flight to North Side, then click on the "flexible dates" box for a list of prices for nearby days. Another helpful hint? Book in advance. To give you an idea of fares, was the best price for a flight to North Side in the last seven days.
How much is a flight to North Side?
One-way flights departing from () sold for as little as in the last seven days. During this period, the cost of a return airfare to North Side ranged between and . If you spot a good deal, book fast — these fares don't hang around.
What are the most popular airports to fly into in North Side?
North Side's primary gateway is O'Hare Intl. Airport (ORD). Get your exciting journey underway by locking in a seat on one of the 33491 flights a month to this destination.
When is the cheapest time to fly to North Side?
If you can be flexible with your travel dates to North Side, depart early in the week. The most affordable day to take off is usually Tuesday, closely followed by Monday. Saturday is typically the costliest day, with many holiday makers preferring to fly on the weekend.
How much is a plane ticket to North Side?
Airfares to North Side varied from to in the last seven days. Generally, the quicker you book the better the deal.
Which airlines with flights to North Side employ COVID-19 cleanliness policies?
As travel borders start to open, most airlines have resumed services with new strategies including social distancing and staggered boarding and disembarkation. Here's what a number of carriers are doing to ease the spread of COVID-19:
  • United Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.