Northwest Side Holidays from AU$1,318

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The Latest Northwest Side Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Kinzie Hotel

Kinzie Hotel

4 out of 5
Downtown Chicago
Price was AU$1,661, price is now AU$1,318 per person
AU$1,318
per person
4 June - 7 June
found 1 day ago
Return flight included
Las Vegas (LAS) to Chicago (ORD)
9.2/10 Wonderful! (2,091 reviews)
Great area, hotel was nice, staff was excellent

Reviewed on 21 Mar 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was AU$2,235, price is now AU$1,397 per person
AU$1,397
per person
4 June - 7 June
found 1 day ago
Return flight included
Las Vegas (LAS) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
The property is located within a short walk to the Magnificent Mile, restaurants, the north side of the river, Target, AMC theaters, Walgreens, Northwestern Medicine and the bus line. They have figured out convenience. The property was as beautiful as it was immaculate. The rooms were spacious with a fantastic shower and amazing shampoo, conditioner and lotion! I’ve even looked into buying it for my home. The breakfast buffet was unbelievable! The food was plentiful with more options than I thought possible. Even more impressive was the breakfast staff who kept the tables clean and the food available, hot and fresh. The hosts took a special interest in knowing the guests, and I know this first hand. My birthday fell during our stay, and the breakfast staff had a table waiting for my family and presented a birthday brownie with the words “Happy Birthday” written in chocolate sauce! Unfortunately, I had unexpectedly been hospitalized for emergency surgery so I missed the opportunity to experience their grand gesture, but the first morning I walked into breakfast after being discharged from the hospital, the host having never see me, asked if my family had given me the brownie. l was blown away! Will I stay again? Without any hesitation!!! Excellent choice!!

Reviewed on 22 Mar 2026

Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
Downtown Chicago
Price was AU$2,071, price is now AU$1,574 per person
AU$1,574
per person
4 June - 7 June
found 1 day ago
Return flight included
Las Vegas (LAS) to Chicago (ORD)
8.8/10 Excellent! (1,894 reviews)
Beautiful views from room. Friendly helpful staff.

Reviewed on 20 Mar 2026

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

4.5 out of 5
Downtown Chicago
Price was AU$1,795, price is now AU$1,377 per person
AU$1,377
per person
4 June - 7 June
found 1 day ago
Return flight included
Las Vegas (LAS) to Chicago (ORD)
9.2/10 Wonderful! (1,414 reviews)
Check in was quick and easy, room was clean and spacious

Reviewed on 9 Mar 2026

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was AU$1,703, price is now AU$1,335 per person
AU$1,335
per person
4 June - 7 June
found 1 day ago
Return flight included
Las Vegas (LAS) to Chicago (ORD)
9/10 Wonderful! (3,314 reviews)
Clean room nice staff, beautiful property. Enjoyed the deluxe room

Reviewed on 20 Mar 2026

Our guide on where to stay in Northwest Side

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

2 out of top 10 points of interest in this area

Irving Park is well liked for its restaurants and live music. If you're hoping to get in some sightseeing, Milwaukee Avenue and Irish American Heritage Center are top spots, and you can jump on the metro at Irving Park Station (Blue Line) or Addison Station (Blue Line) to get around.

Find hotels in Irving Park

Northwest Side Holiday

Northwest Side Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)

Our pick of the best Northwest Side Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$194 per night from 30 Mar to 31 Mar
AU$194
30 Mar - 31 Mar
includes taxes & fees
8/10 Very Good! (9,982 reviews)
It’s an old hotel. It needs a quality paint job and new carpets in the hallways among many other things. But the lake view rooms makes up for a lot of what’s missing.

Reviewed on 22 Mar 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$261 per night from 6 Apr to 7 Apr
AU$261
6 Apr - 7 Apr
includes taxes & fees
9.4/10 Exceptional! (3,590 reviews)
The property is located within a short walk to the Magnificent Mile, restaurants, the north side of the river, Target, AMC theaters, Walgreens, Northwestern Medicine and the bus line. They have figured out convenience. The property was as beautiful as it was immaculate. The rooms were spacious with ...

Reviewed on 22 Mar 2026

Hotel Riu Plaza Chicago
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$218 per night from 29 Mar to 30 Mar
AU$218
29 Mar - 30 Mar
includes taxes & fees
8.6/10 Excellent! (5,765 reviews)
Spent three nights with husband and teenage son over spring break. Young man who checked us in was not friendly, did not mention happy hour, or breakfast. He did not give us any information except room number. Breakfast staff was nice and polite. Recommend getting to breakfast early or there will ...

Reviewed on 22 Mar 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 5,067 properties in Northwest 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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Discover the most popular places to visit in Northwest Side

View of Chicago skyline at sunrise.

Naval Base Great Lakes

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
Navy Pier featuring a sunset and rides

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
Millennium Park showing modern architecture, a city and street scenes

Millennium Park

4.5/5(73 reviews)

One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.

Millennium Park

What to do in Northwest 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$62
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
Chicago C3® : Save on admission to your choice of 3 top attractactions

Chicago C3® by CityPASS®

AU$150
per adult
88% of travellers recommend
Chicago C3® by CityPASS®
See all activities in Northwest Side

Frequently asked questions

Can I cancel my flight booking to Northwest Side due to COVID-19?
Our Customer Service Portal is where you can find information about changing or cancelling your flight due to COVID-19. Before purchasing your tickets, it's smart to check the terms and conditions of your airfare too.
What's the best way to find cheap flights to Northwest Side that have flexible change policies?
We know that things can change from one minute to the next, so booking a flexible airfare with Expedia is always a wise idea. Simply mark the "No change fee" box directly below the "Flexible change policies" filter. Your low-cost, flexible flight to Northwest Side is only a few clicks away.
What are some of the general tips for travellers to Northwest Side during the COVID-19 outbreak?
With the continuation of the COVID-19 outbreak, travelling now comes with more challenges than in the past. Cast your eye over these worthwhile tips before boarding your flight to Northwest Side:
  • Before you book a flight, check if any travel restrictions apply — in both your origin and destination. Get the latest updates by reviewing government and airport websites.
  • When you pass through airport checkpoints, keep your face mask on. You will be asked to briefly lower it for identification purposes. Passengers who refuse to wear a face mask may face civil penalties and may also be denied boarding.
  • Instead of handing a TSA officer your boarding pass, position it directly on the scanner yourself. Then, hold it up for inspection.
  • You can now take one container of hand sanitizer up to 12 oz (350 ml) in your carry-on luggage. This will need to be removed for screening.
  • To reduce handling during the screening process, place items such as your keys, wallet, phone and belt into your carry-on rather than into the bins.
  • If you're planning to take food through the security checkpoint, put it in a clear plastic bag and then into a scanning bin. This reduces the likelihood that a TSA employee will need to touch your food container or carry-on bag for closer inspection.

Which airlines fly to Northwest Side?
Arrange your ticket with American Airlines and then begin working on your Northwest Side itinerary. This popular carrier offers 13307 flights a month to O'Hare Intl. Airport (ORD), a main gateway.
How can I find cheap tickets to Northwest Side?
An effective strategy for getting your hands on cheap fares is to be flexible with your travel dates. Begin with searching for your flight to Northwest Side, then click on the "flexible dates" box for a list of prices for nearby days. Another good tip? Book ahead of time. For an idea of costs, was the lowest price for a flight to Northwest Side in the last seven days.
How much is a flight to Northwest Side?
If you were travelling one way from (), you could've nabbed a cheap ticket for in the last seven days. Round-trip flights to Northwest Side ranged from to during this same period.
What are the most popular airports to fly into in Northwest Side?
Get ready to pack your suitcase and jet into O'Hare Intl. Airport (ORD), Northwest Side's primary flight hub. Book a fare on one of the 33491 flights that land at this popular destination every month.
When is the cheapest time to fly to Northwest Side?
Fly out on a Tuesday to boost your odds of landing the cheapest flight to Northwest Side. Mondays are usually the second most affordable day to take off. Saturday is generally the most expensive day to fly anywhere.
How much is a plane ticket to Northwest Side?
In the last seven days, fares to Northwest Side fluctuated between and . The early bird catches the worm, so snap up a bargain today.
Which airlines with flights to Northwest Side employ COVID-19 cleanliness policies?
As travel bans start to lift, many airlines are now servicing flights with new strategies including physical distancing and staggered boarding and disembarkation. Here's what some carriers are doing to help combat 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.