Near West Side Holidays from NZ$2,594

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Top Holiday Package Deals in Near West Side

Price found within the past 48 hours. Click for updated prices.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was NZ$3,219, price is now NZ$2,594 per person
NZ$2,594
per person
22 Dec - 27 Dec
found 11 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (1,110 reviews)
A great location, a fabulous building, and a delightful room. The one mystery was a background thumping noise that persisted throughout the stay. Fortunately, didn't disturb sleep. The reception staff sloughed off any knowledge or interest in the cause, but we couldn't imagine that the source was an unknown to hotel staff, and potentially fixable.

Reviewed on 12 Nov 2025

The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Price was NZ$4,299, price is now NZ$2,678 per person
NZ$2,678
per person
22 Dec - 27 Dec
found 11 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
8.8/10 Excellent! (1,070 reviews)
Great trip! Will stay again.

Reviewed on 2 Nov 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was NZ$4,432, price is now NZ$3,407 per person
NZ$3,407
per person
22 Dec - 27 Dec
found 11 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9.6/10 Exceptional! (1,006 reviews)
This is a beautiful hotel with lots of amenities that feel kind of luxurious. We especially loved the huge tub in our room. Also, the staff was amazing. One gripe we had is that we paid quite a bit more for a lake view room and we were on the eighth floor, which did not really afford much of a view. We called the front desk to see if we could get a higher floor and they said there was nothing available, but they did bring us a bottle of wine to compensate. I know someone has to be on the lower floors, but it seems that if you are going to pay more for a view they should make sure you are on a higher floor. Other than that, we would definitely stay here again and would recommend!

Reviewed on 20 Oct 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was NZ$3,323, price is now NZ$2,689 per person
NZ$2,689
per person
22 Dec - 27 Dec
found 11 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9/10 Wonderful! (367 reviews)
Property was clean, centrally located with wonderful staff. Will definitely stay again.

Reviewed on 9 Nov 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was NZ$3,062, price is now NZ$2,601 per person
NZ$2,601
per person
22 Dec - 27 Dec
found 11 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9.2/10 Wonderful! (303 reviews)
I love the decor and it was very clean. My only problem is they did not clean the room every day other than that is was very clean facility. Very safe location.

Reviewed on 28 Oct 2025

Our guide on where to stay in Near West Side

Find the best Near West Side areas and neighborhoods for the activities you enjoy most. Learn more about Near West Side
Downtown Chicago featuring a city

Downtown Chicago

4 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 Near 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$187 per night from 23 Nov to 24 Nov
NZ$187
23 Nov - 24 Nov
includes taxes & fees
8.8/10 Excellent! (1,661 reviews)
The room was clean and nice but, I could hear all going on outside. They need soundproof glass on the balcony door. Only window in the whole room. Even 14 floors up the noise was bad. Very nice staff.

Reviewed on 9 Nov 2025

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$644 per night from 13 Dec to 14 Dec
NZ$644
13 Dec - 14 Dec
includes taxes & fees
9/10 Wonderful! (1,262 reviews)
Perfect stay and location. Room was clean and just what we needed. It’s nothing special

Reviewed on 11 Nov 2025

The Emily Hotel
Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

2.5 out of 5
710 S Seeley Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$181 per night from 7 Dec to 8 Dec
NZ$181
7 Dec - 8 Dec
includes taxes & fees
9.6/10 Exceptional! (315 reviews)
Clean, friendly staff, delicious breakfast, varied breakfast options, doesn’t barge into hotel room during unprecedented times, sizable rooms

Reviewed on 8 Nov 2025

Hampton Inn & Suites Chicago Medical District UIC
See all 4,732 properties in Near 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 Near West Side holiday package cost?
Custom build your Near West Side package from a low NZ$2,594. Choose from any combination of rental cars, flights and hotels to craft the trip you've been dreaming about for ages. Don't forget to add on a few activities!
How do I get a cheap travel package to Near West Side?
Our Near West Side holiday packages mean plenty of savings for the savvy traveller. For the best deals, simply combine your hotel, flights and extras (including tours) into a convenient package. But great bargains are just the beginning of your next big adventure. Book with Expedia and you'll have more than 550 air carriers and 1 000 000 properties around the world to select from. Whatever your budget, there's a package with your name on it.
Where should I stay in Near West Side?
Make sightseeing a breeze by staying just around the corner from Near West Side's big attractions. University of Illinois Chicago and United Centre are two of the most popular.
What are the top hotels in Near West Side?
If it's your first time in Near West Side, lock in a room at Hyatt House Chicago Medical/University District or Hyatt Place Chicago Medical/University District. Both hotels offer comfortable beds and are favourites among lots of travellers.
How far in advance should I book my Near West Side holiday?
It's difficult to pick the best time for airfares, but we usually say the earlier, the better. Plenty of international journeys on Expedia become available to compare up to 12 months in advance. If you're booking late, don't despair. Low prices appear from time to time within a few weeks of departure dates.
What does an Expedia Near West Side travel package include?
Hotels, flights and a cool set of wheels for your road trip adventures. Simply pick and choose your preferred bundle and get access to great discounts. Once you've made your booking, add on a couple of activities and tours and watch your savings pile up. When it comes to creating your Near West Side escape, you're the boss!
What should I know before booking a Near West Side travel package?
A travel package can be easier on the wallet than individually booking all you need for your adventure. For example, bundle your hotels, flights and rental cars and save a tidy sum. Whatever kind of holiday you're planning, you're bound to find a package that's perfect for you.
Can I choose my airline with a Near West Side Expedia holiday package?
Yes, you're in control. Expedia has access to more than 550 partner airlines around the world, so you can design your Near West Side holiday according to your travel needs.
If I'm not able to travel, can I cancel my Near West Side holiday package?
Because we know life can be unpredictable, the answer is yes. For further details, check out our Customer Service Portal. But generally speaking, if you've booked your Near West Side holiday package in the last 24 hours, you may be able to cancel or change it for no charge. Your airline, hotel or car rental company may charge a fee if you made your booking a while ago.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.