Lower West Side Holidays from NZ$3,873

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Top Holiday Package Deals in Lower West Side

Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was NZ$4,297, price is now NZ$3,873 per person
NZ$3,873
per person
3 Aug - 6 Aug
found 1 day ago
Return flight included
Palmerston North (PMR) to Chicago (ORD)
9.4/10 Exceptional! (2,554 reviews)
Great stay; fabulous location, amazing views and access to so much; friendly staff. Super friendly and accommodating housekeeping! Food/bar service took a long long time, every time..long wait to order…long wait to get drinks…long wait to pay bill. Not enough staff behind the bar.

Reviewed on 30 June 2026

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
Downtown Chicago
Price was NZ$6,663, price is now NZ$5,321 per person
NZ$5,321
per person
3 Aug - 6 Aug
found 1 day ago
Return flight included
Palmerston North (PMR) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
The hotel is very clean Good air conditioning The staff is great The bar at the restaurant is very good The location is the best in Chicago Fancy neighborhood

Reviewed on 30 June 2026

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Price was NZ$4,435, price is now NZ$3,900 per person
NZ$3,900
per person
3 Aug - 6 Aug
found 1 day ago
Return flight included
Palmerston North (PMR) to Chicago (ORD)
9.2/10 Wonderful! (1,821 reviews)
My husband and I and my daughter in law stayed at the omni because my son was having surgery at northwestern hospital. Is surgery was at 7:30 am and lasted almost 8 hours check in was not until 4, but they really understood our situation they were able to get into our room at noon. So we can rest. Everyone from the greeders at the door the front desk was tremendously helpful in our situation. A room was clean, check-up process with so easy.I highly recommend staying at this hotel.

Reviewed on 1 July 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was NZ$4,523, price is now NZ$3,985 per person
NZ$3,985
per person
3 Aug - 6 Aug
found 1 day ago
Return flight included
Palmerston North (PMR) to Chicago (ORD)
9.2/10 Wonderful! (1,323 reviews)
Very unique motif

Reviewed on 1 July 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was NZ$5,044, price is now NZ$4,520 per person
NZ$4,520
per person
3 Aug - 6 Aug
found 1 day ago
Return flight included
Palmerston North (PMR) to Chicago (ORD)
9.2/10 Wonderful! (504 reviews)
The staff was extremely friendly and flexible regarding scheduling; this place is amazing.

Reviewed on 1 July 2026

Our guide on where to stay in Lower West Side

Find the best Lower West Side areas and neighborhoods for the activities you enjoy most. Learn more about Lower West Side
A busy city street with tall buildings, a bus, and cars.

Downtown Chicago

5 out of top 10 points of interest in this area

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Find hotels in Downtown Chicago

Our pick of the best Lower West 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 NZ$312 per night from 2 July to 3 July
NZ$312
2 July - 3 July
includes taxes & fees
8/10 Very good! (10,185 reviews)
"This place was really horrible! The shower was cold as hell and the front desk didn't do anything to help. The room was not wiped down properly and I left first thing on the A.M. when I told the front desk about my stay, they did nothing to fix the issue or reimburse me a portion of my money. I came ..."

Reviewed on 1 July 2026

Congress Plaza Hotel
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$379 per night from 5 July to 6 July
NZ$379
5 July - 6 July
includes taxes & fees
9.2/10 Wonderful! (1,825 reviews)
"My husband and I and my daughter in law stayed at the omni because my son was having surgery at northwestern hospital. Is surgery was at 7:30 am and lasted almost 8 hours check in was not until 4, but they really understood our situation they were able to get into our room at noon. So we can rest. ..."

Reviewed on 1 July 2026

Omni Chicago Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$396 per night from 6 July to 7 July
NZ$396
6 July - 7 July
includes taxes & fees
9/10 Wonderful! (4,476 reviews)
"Bedsheets had stains upon arrival and the shower & sink faucet dials were loose."

Reviewed on 1 July 2026

Hilton Chicago/Magnificent Mile Suites
See all 4,548 properties in Lower 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.

Frequently asked questions

How much does a Lower West Side holiday package cost?
Choose from any combination of hotels, flights and car rentals, and you can be holidaying in Lower West Side from just NZ$3,873. And the more you bundle, the more cash you save. The holiday of your dreams has never been so affordable.
How do I get a cheap travel package to Lower West Side?
Combine your bookings with Expedia to save on your next exciting adventure. With over 550 partner airlines and 1 000 000 properties throughout the world, your Lower West Side holiday package can be customized exactly to suit your travel style. With all that extra money, why not throw in a few interesting tours and activities? It's an easy way to unlock even more discounts. Your dream holiday in Lower West Side is closer than you thought!
Where should I stay in Lower West Side?
Most people who travel to Lower West Side include both University of Illinois Chicago and United Centre on their bucket lists. Why not reserve a hotel as close as possible to these iconic attractions?
How far in advance should I book my Lower West Side holiday?
Reserving your seat early with Expedia means one less thing to have to worry about. Most carriers advertise tickets up to a year in advance. This is often the cheapest time to book. If circumstances have left you booking late, low prices to Lower West Side sometimes become available a few weeks before departure.
What does an Expedia Lower West Side travel package include?
It comes down to what you're after. If you're travelling alone, you might decide to combine flights and hotels. Taking the whole family to Lower West Side? A travel package including flights, hotels and rental cars might be a better fit. Expedia gives you the freedom to build your own travel package.
What should I know before booking a Lower West Side travel package?
You can save a tidy sum by combining your hotels, airfares and rental cars. Once you've created your package, add on fun stuff like sightseeing tours or experiences. Your next awesome holiday is only a couple of clicks away.
Can I choose my airline with a Lower West Side Expedia holiday package?
Yes — that's the beauty of an Expedia holiday package. You're the boss! We have access to more than 550 partner airlines across the globe, so you have loads of choice when putting together your Lower West Side adventure.
If I'm not able to travel, can I cancel my Lower West Side holiday package?
We totally understand — life can throw you the odd curveball. If you've locked in a Lower West Side holiday package and have to cancel or amend it, we can help. It's always worth taking a look at our Customer Service Portal first for information. But in general, if you've booked your package in the last 24 hours, you may be able to amend or cancel your itinerary free of charge. If it's more than 24 hours, your hotel, airline or car rental company may impose a charge.

Stay near popular Lower West Side attractions

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.
See properties

Activities

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

NZ$41
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

NZ$68
per adult
92% of travellers recommend
Art Institute of Chicago
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

NZ$78
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.