North Side Holidays from AU$3,052

Book a Hotel + Flight or Car together to unlock savings

Photo by Vincent Ramundo

  • Plan, book, travel with confidence

  • Better together

    Save up to AU$2,500 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

The Latest North Side Holiday Deals

Price found within the past 48 hours. Click for updated prices.
LakeWood Inn & Suites

LakeWood Inn & Suites

2 out of 5
Price was AU$3,140, price is now AU$3,052 per person
AU$3,052
per person
2 July - 8 July
found 1 day ago
Return flight included
Sydney (SYD) to Chicago (ORD)
7.2/10 Good! (73 reviews)
Property was nice...exactly what i expected...beds were great..slept like a baby

Reviewed on 20 Oct 2025

The Morris Estate

The Morris Estate

4 out of 5
Price was AU$4,651, price is now AU$4,107 per person
AU$4,107
per person
2 July - 8 July
found 1 day ago
Return flight included
Sydney (SYD) to Chicago (ORD)
10/10 Exceptional! (128 reviews)
Had a great stay! Great place!

Reviewed on 4 May 2026

The Brewery Lodge Hotel

The Brewery Lodge Hotel

3.5 out of 5
Price was AU$3,852, price is now AU$3,593 per person
AU$3,593
per person
2 July - 8 July
found 1 day ago
Return flight included
Sydney (SYD) to Chicago (ORD)
9/10 Wonderful! (831 reviews)
Everything was great other than the bed being super hard. It felt cozy like I was staying at someone’s grandmas house.

Reviewed on 11 May 2026

Holiday Inn Express Hotel & Suites Niles by IHG

Holiday Inn Express Hotel & Suites Niles by IHG

2.5 out of 5
Price was AU$3,684, price is now AU$3,526 per person
AU$3,526
per person
2 July - 8 July
found 1 day ago
Return flight included
Sydney (SYD) to Chicago (ORD)
9/10 Wonderful! (749 reviews)
Staff and breakfast was great.

Reviewed on 27 Apr 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

6 out of top 10 points of interest in this area

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$188 per night from 26 May to 27 May
AU$188
26 May - 27 May
includes taxes & fees
8.8/10 Excellent! (1,018 reviews)
Such a cozy place with a very friendly and accessible staff.

Reviewed on 12 May 2026

The Majestic Hotel
Hotel Lincoln

Hotel Lincoln

4 out of 5
1816 N Clark Street Chicago IL
The price is AU$224 per night from 25 May to 26 May
AU$224
25 May - 26 May
includes taxes & fees
7.8/10 Good! (1,101 reviews)
Ron, at the front desk was so kind and helpful - the others, not so much. The first room was ok but a little funky and old for the price, the 2nd room was much better with plenty of room for 2. Can’t beat the location! Rooftop bar was pleasant. I would stay there again but make sure I got the right ...

Reviewed on 11 May 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$267 per night from 25 May to 26 May
AU$267
25 May - 26 May
includes taxes & fees
8.6/10 Excellent! (1,010 reviews)
There is a convenient parking lot (not free) close to the hotel. Not sure about air conditioning - probably does not have.

Reviewed on 12 May 2026

The Willows Hotel
See all 562 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
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
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$37
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

AU$61
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
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
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.

Explore a world of travel with Expedia

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