Near West Side Holidays from AU$1,530

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Your Near West Side Holiday

Organising your next getaway just got a whole lot easier with a holiday package to Near West Side. Enjoy all this neighbourhood has to offer while making nice memories you won't forget. When it's time to sightsee, you'll find lots of top attractions nearby including University of Illinois Chicago, United Centre and Anna and Frederick Douglass Park. Visit one, two or more during your trip to Near West Side. Stop daydreaming and start doing. When you're ready to book your dream holiday to Near West Side, Expedia will help get you there.

Top Holiday Package Deals in Near West Side

Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was AU$1,761, price is now AU$1,530 per person
AU$1,530
per person
10 Feb - 13 Feb
found 2 hours ago
Return flight included
Brisbane (BNE) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
great staff...loved our stay.

Reviewed on 22 Nov 2025

Chicago luxury home suites

Chicago luxury home suites

2 out of 5
Downtown Chicago
Price was AU$3,991, price is now AU$3,180 per person
AU$3,180
per person
10 Feb - 13 Feb
found 2 hours ago
Return flight included
Brisbane (BNE) to Chicago (ORD)
10/10 Exceptional! (1 review)
Great service and communication throughout my entire stay. Very clean and easy to access to everything that i needed. Even though it was a short stay but had a comfortable and pleasant stay. Everything was available for me before i arrived. Thank you really. Great job.

Reviewed on 26 Nov 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was AU$2,446, price is now AU$1,966 per person
AU$1,966
per person
10 Feb - 13 Feb
found 2 hours ago
Return flight included
Brisbane (BNE) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Mostly great. The pull out sofa bed is not usable as it’s so uncomfortable. So then they charge $50/night for each rollaway. Thats not a good solution.

Reviewed on 28 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 AU$2,255, price is now AU$1,813 per person
AU$1,813
per person
10 Feb - 13 Feb
found 2 hours ago
Return flight included
Brisbane (BNE) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
The room was beautiful and clean and a good city view of the city

Reviewed on 26 Nov 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was AU$1,827, price is now AU$1,624 per person
AU$1,624
per person
10 Feb - 13 Feb
found 2 hours ago
Return flight included
Brisbane (BNE) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
I had an amazing stay at The Pendry Chicago. The hotel is gorgeous, modern, and feels truly high-end without trying too hard. My room was super clean, comfortable, and quiet—honestly one of the best sleep setups I’ve had in a hotel. The staff made the whole experience even better. Everyone I talked to was friendly, helpful, and actually seemed to enjoy their jobs. The lobby bar and restaurant were great too, and the whole vibe of the place is relaxed but still upscale. The location made it easy to get around the city, but I kept finding myself wanting to head back early just to enjoy the hotel. I’d definitely stay here again and recommend it to anyone visiting Chicago.

Reviewed on 30 Nov 2025

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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

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 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 AU$228 per night from 21 Dec to 22 Dec
AU$228
21 Dec - 22 Dec
includes taxes & fees
8.8/10 Excellent! (1,708 reviews)
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Reviewed on 27 Nov 2025

Crowne Plaza Chicago West Loop by IHG
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 AU$156 per night from 7 Dec to 8 Dec
AU$156
7 Dec - 8 Dec
includes taxes & fees
9.6/10 Exceptional! (348 reviews)
Room was very clean and comfortable. Would have appreciated a disposable bathroom glass for use when brushing teeth or taking a pill. Had to take a cup from the coffee station.

Reviewed on 26 Nov 2025

Hampton Inn & Suites Chicago Medical District UIC
The Emily Hotel

The Emily Hotel

4 out of 5
311 North Morgan Street Chicago IL
The price is AU$680 per night from 1 Dec to 2 Dec
AU$680
1 Dec - 2 Dec
includes taxes & fees
9/10 Wonderful! (1,280 reviews)
Staff was awesome

Reviewed on 27 Nov 2025

The Emily Hotel
See all 4,841 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.
All Inclusive Holidays
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Frequently asked questions

How much does a Near West Side holiday package cost?
Custom build your Near West Side package from a low AU$1,530. 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.

Discover the most popular places to visit in Near West Side

United Center

United Center

Catch an event at United Center during your trip to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theatre scene.

United Center
University of Illinois Chicago

University of Illinois Chicago

Enjoy the student vibe at University of Illinois Chicago during your visit to Chicago. Stroll along the riverfront or experience the acclaimed art galleries in this vibrant area.

University of Illinois Chicago

Activities

Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

AU$69
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Art Institute of Chicago

Art Institute of Chicago

AU$62
per adult
92% of travellers recommend
Art Institute of Chicago
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

AU$38
per adult
84% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
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.