West Side Holidays from NZ$3,018

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The Latest West 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 NZ$3,755, price is now NZ$3,018 per person
NZ$3,018
per person
14 Aug - 19 Aug
found 21 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
8.2/10 Very Good! (2,744 reviews)
Hotel Felix was in a fantastic location. The staff were very friendly. Our room on the 9th floor with 2 double beds was small, with only a mini fridge. The curtains were old and difficult to open and close. The WiFi would drop or was very slow. The television also provided issues, turning off or to the starting screen, multiple times. The hotel offered only coffee/tea and fresh fruit until 9am. The staff made our stay more enjoyable.

Reviewed on 8 June 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was NZ$5,787, price is now NZ$4,480 per person
NZ$4,480
per person
14 Aug - 19 Aug
found 21 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.6/10 Exceptional! (1,893 reviews)
We love the pool, cleanliness in the room .Friendly staff

Reviewed on 6 June 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was NZ$4,504, price is now NZ$3,493 per person
NZ$3,493
per person
14 Aug - 19 Aug
found 21 hours ago
Return flight included
Auckland (AKL) 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

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Price was NZ$6,320, price is now NZ$4,955 per person
NZ$4,955
per person
14 Aug - 19 Aug
found 21 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.8/10 Exceptional! (1,002 reviews)
The pool was a true lap pool. The Fitness Center and the locker room was exquisite.

Reviewed on 8 June 2026

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Price was NZ$3,997, price is now NZ$3,250 per person
NZ$3,250
per person
14 Aug - 19 Aug
found 21 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.2/10 Wonderful! (1,791 reviews)
beautiful room city view excellent location quiet and comfortable

Reviewed on 9 June 2026

Our guide on where to stay in West Side

Find the best West Side areas and neighborhoods for the activities you enjoy most. Learn more about West Side
Blue Hour evening cityscape in West Loop neighborhood. Long exposure, nightscape architecture. Main street in Chicago, streets in Illinois.

West Loop

1 out of top 10 points of interest in this area

Consider a visit to The Old Post Office and take some time to enjoy the abundant dining options during your time in West Loop. If you want to see more of the city, jump on the metro at Racine Station or Ogilvie Transportation Center.

Find hotels in West Loop

West Side Holiday

Our pick of the best West Side Hotel Deals

Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street Chicago IL
Fully refundable
The price is NZ$321 per night from 1 July to 2 July
NZ$321
1 July - 2 July
includes taxes & fees
9/10 Wonderful! (2,246 reviews)
"It was a great choice if you want to be in the west loop area. Easy to walk to places. Clean and great staff!"

Reviewed on 8 June 2026

Crowne Plaza Chicago West Loop by IHG
The Emily Hotel

The Emily Hotel

4 out of 5
311 North Morgan Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$502 per night from 28 June to 29 June
NZ$502
28 June - 29 June
includes taxes & fees
9.2/10 Wonderful! (1,327 reviews)
"Rooftop Movie theater looked fun during the daytime, but wasn’t committed enough to buy a ticket after sunset. Rooms were fine. Coffee shop was short-staffed the day I was there - to the point I gave up and moved on. The staff I ran into in the hotel from housekeeping to front desk to bell staff ..."

Reviewed on 8 June 2026

The Emily Hotel
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3 out of 5
506 West Harrison Street Chicago IL
The price is NZ$343 per night from 2 July to 3 July
NZ$343
2 July - 3 July
includes taxes & fees
8.6/10 Excellent! (1,022 reviews)
"Just not nice."

Reviewed on 9 June 2026

Holiday Inn & Suites Chicago - Downtown by IHG
See all 756 properties in West 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.

Discover the most popular places to visit in West Side

Garfield Park Conservatory

Garfield Park Conservatory

The huge glass-roofed rooms bring some amazing landscapes, and spectacular plants, to western Chicago.

Garfield Park Conservatory

Anna and Frederick Douglass Park

After visiting Anna and Frederick Douglass Park, make a plan to see the other sights and activities in Chicago. Experience the entertainment choices and acclaimed theatre scene in this vibrant area.

Anna and Frederick Douglass Park

Canalport Riverwalk Park

After visiting Canalport Riverwalk Park, make a plan to see the other sights and activities in Chicago. Experience the area's art scene and festivals.

Canalport Riverwalk Park

What to do in West Side

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

NZ$45
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

NZ$77
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
Art Institute of Chicago

Art Institute of Chicago

NZ$67
per adult
92% of travellers recommend
Art Institute of Chicago
See all activities in West Side

Frequently asked questions

Can I cancel my flight booking to West Side due to COVID-19?
Our Customer Service Portal has useful information about changing or cancelling your flight due to COVID-19. Before booking your tickets, it's wise to check the terms and conditions of your chosen airline too.
What's the best way to find cheap flights to West Side that have flexible change policies?
At Expedia, we've been channeling our inner yoga master to get you the most flexible airfares around town. Simply check the "No change fee" box directly beneath the filter subheading "Flexible change policies" to find your dream flight to West Side.
What are some of the general tips for travellers to West Side during the COVID-19 outbreak?
COVID-19 has led to substantial changes to how we travel. If you're planning a trip to West Side, the following tips will help you navigate this new travelling reality:
  • Before booking anything, check if any travel bans or restrictions apply — in both your destination and origin. Get the latest updates by reviewing government travel advisories.
  • Requirements state you must wear a face mask at the airport, including at screening checkpoints. Be ready to lower your mask for ID purposes when asked by a TSA employee.
  • Rather than handing a TSA agent your boarding pass, place it directly on the reader yourself. When that's done, hold it up for inspection.
  • TSA is now allowing passengers to take one container of hand sanitizer, up to 12 oz (350 ml) in size, in carry-on baggage. This will need to be removed from your bag for screening.
  • Place any personal items (like your phone, wallet and keys) in your carry-on rather than a bin to minimize handling during the screening process.
  • Separate any food you have for X-ray scanning. Food items often trigger the alarm. Putting them in a clear plastic bag and into a bin reduces the need for a TSA agent to touch and inspect your belongings.

Which airlines fly to West Side?
Let American Airlines take you there. This leading carrier schedules 13307 flights each month to O'Hare Intl. Airport (ORD), a West Side gateway.
How can I find cheap tickets to West Side?
A useful strategy for nabbing cheap fares is to be flexible with your travel dates. Start by searching for your flight to West Side, then click on the "flexible dates" box for a list of prices for nearby days. Another handy tip? Book well ahead of time. To give you an idea of fares, was the lowest price for a flight to West Side in the last seven days.
How much is a flight to West Side?
If you were flying one way from (), you could've snapped up an affordable ticket for in the last seven days. Round-trip flights to West Side ranged from only to over the same period.
What are the most popular airports to fly into in West Side?
West Side's main entry point is O'Hare Intl. Airport (ORD). Get your next big journey underway by securing an airfare on one of the 33491 flights a month to this destination.
When is the cheapest time to fly to West Side?
Flying on a Tuesday, followed by a Monday, is generally the best way to get the cheapest deal. Stay away from the weekends if you can, because Saturday is typically the most expensive day. Spend the money you saved enjoying yourself in West Side instead!
How much is a plane ticket to West Side?
In the last seven days, fares cost between and . Scroll through our amazing deals to West Side, make a booking and then get ready for your getaway!
Which airlines with flights to West Side employ COVID-19 cleanliness policies?
To reduce contact between passengers and flight attendants during the global COVID-19 pandemic, most reputable airlines have taken social distancing and other strategies to the skies. Just a few of these are:
  • 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.