Northwest Side Holidays from AU$503

Book a Hotel + Flight or Car together to unlock savings

  • 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 Northwest Side Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was AU$655, price is now AU$503 per person
AU$503
per person
5 Aug - 7 Aug
found 18 hours ago
Return flight included
New York (LGA) to Chicago (ORD)
8.2/10 Very Good! (2,683 reviews)
If you’re up for walking, this hotel is a great place to stay close enough to most things.

Reviewed on 8 May 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was AU$1,297, price is now AU$962 per person
AU$962
per person
5 Aug - 7 Aug
found 18 hours ago
Return flight included
New York (LGA) to Chicago (ORD)
9.4/10 Exceptional! (1,863 reviews)
Incredible everything

Reviewed on 8 May 2026

Le Méridien Essex Chicago

Le Méridien Essex Chicago

4 out of 5
Downtown Chicago
Price was AU$759, price is now AU$575 per person
AU$575
per person
5 Aug - 7 Aug
found 18 hours ago
Return flight included
New York (LGA) to Chicago (ORD)
8.8/10 Excellent! (1,003 reviews)
Staff was attentive and friendly. Atmosphere was welcoming. Restaurant had a great selection food was good and prices reasonable. Rooms were comfy.

Reviewed on 23 Apr 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was AU$957, price is now AU$744 per person
AU$744
per person
5 Aug - 7 Aug
found 18 hours ago
Return flight included
New York (LGA) to Chicago (ORD)
9/10 Wonderful! (3,293 reviews)
Having stayed in the lovely Swissotel Bosphorus/Istanbul, I was hesitant to compare Swissotel experience & hope Chicago would be as good. No. Not even close. The elevated Swissotel brand is not represented here well in this building at all. The valet is $87! Self park is $70 and the self park area doesn’t even have an elevator up to the lobby, you have to walk through a dark, confusing, and claustrophobic garage to stairs then to elevator. Staff were tactful & kind, it’s just the building is old, needs renovation, & the room air is stuffy. A positive bright light was the stunning view from the gym and the lobby ambience & smell.

Reviewed on 6 May 2026

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

3.5 out of 5
Downtown Chicago
Price was AU$792, price is now AU$637 per person
AU$637
per person
5 Aug - 7 Aug
found 18 hours ago
Return flight included
New York (LGA) to Chicago (ORD)
9.2/10 Wonderful! (1,392 reviews)
Nice location nestled I'm the middle of it all. Great stay the staff was communicative.

Reviewed on 7 May 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
EyeEm Custom Shoots Q4 2018

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

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$561 per night from 7 June to 8 June
AU$561
7 June - 8 June
includes taxes & fees
8.2/10 Very Good! (2,697 reviews)
great location

Reviewed on 9 May 2026

Hotel Felix River North/Magnificent Mile
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$219 per night from 10 May to 11 May
AU$219
10 May - 11 May
includes taxes & fees
8/10 Very Good! (10,189 reviews)
Room was clean, coffee maker didn’t work but was replaced quickly. Staff all very helpful, especially Steve the doorman/security. Very helpful getting us a cab!

Reviewed on 8 May 2026

Congress Plaza Hotel
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$208 per night from 25 May to 26 May
AU$208
25 May - 26 May
includes taxes & fees
8.8/10 Excellent! (5,187 reviews)
As soon as we arrived Hotel Staff was very friendly and helpful. Valet parking was very convenient.

Reviewed on 9 May 2026

River Hotel
See all 5,066 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.
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 Northwest Side

Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

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

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

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$38
per adult
88% 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
Art Institute of Chicago

Art Institute of Chicago

AU$56
per adult
92% of travellers recommend
Art Institute of Chicago
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.

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.