Near West Side Holidays from AU$3,640

Book a Hotel + Flight or Car together to unlock savings

Photo by throwingsofas

  • Plan, book, travel with confidence

  • Better together

    Save up to AU$703 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

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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was AU$4,290, price is now AU$3,640 per person
AU$3,640
per person
18 June - 25 June
found 23 hours ago
Return flight included
Melbourne (MEL) to Chicago (ORD)
8.2/10 Very Good! (2,604 reviews)
Room was slightly small and there was no microwave. But for the most part enjoyed my stay.

Reviewed on 15 Apr 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was AU$6,811, price is now AU$5,560 per person
AU$5,560
per person
18 June - 25 June
found 23 hours ago
Return flight included
Melbourne (MEL) to Chicago (ORD)
9.4/10 Exceptional! (1,848 reviews)
Beautiful facility, excellent service, professional staff, delicious food!

Reviewed on 7 Apr 2026

Kinzie Hotel

Kinzie Hotel

4 out of 5
Downtown Chicago
Price was AU$6,062, price is now AU$5,097 per person
AU$5,097
per person
18 June - 25 June
found 23 hours ago
Return flight included
Melbourne (MEL) to Chicago (ORD)
9.2/10 Wonderful! (2,090 reviews)
Spotless room and a comfortable bed. Can't beat the location. Room was not super soundproofed, but not the worst I've ever experienced.

Reviewed on 15 Apr 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was AU$7,621, price is now AU$6,416 per person
AU$6,416
per person
18 June - 25 June
found 23 hours ago
Return flight included
Melbourne (MEL) to Chicago (ORD)
9.2/10 Wonderful! (902 reviews)
The check in process was a little crazy, can’t say I have ever needed a background check to stay somewhere so it was a bit time consuming although I suppose good to know safety is a priority. View from property was the best part hands down! Cost of overall stay was great deal, parking for $65 a night was a bit disappointing because it is nice to have it on site. Overall would stay again.

Reviewed on 14 Apr 2026

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

3.5 out of 5
Downtown Chicago
Price was AU$4,891, price is now AU$4,141 per person
AU$4,141
per person
18 June - 25 June
found 23 hours ago
Return flight included
Melbourne (MEL) to Chicago (ORD)
9.2/10 Wonderful! (1,409 reviews)
Great location and converted old Virgin Hotel. Room was fine and hotel basics were fine. There wasn’t any room service daily or for my 3 night stay. There was a strike for housekeepers and they were LOUD out front everyday. Not sure what the hotel fee was for on top of Expedia hotel charge was for, they gave me 2 waters the first day and that was it. They also upsell their vacation club/time share a lot, kinda odd.

Reviewed on 14 Apr 2026

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

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$221 per night from 26 Apr to 27 Apr
AU$221
26 Apr - 27 Apr
includes taxes & fees
9/10 Wonderful! (2,092 reviews)
No coffee in coffee pot no breakfast

Reviewed on 16 Apr 2026

Crowne Plaza Chicago West Loop by IHG
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3 out of 5
506 West Harrison Street Chicago IL
Fully refundable
The price is AU$210 per night from 26 Apr to 27 Apr
AU$210
26 Apr - 27 Apr
includes taxes & fees
8.6/10 Excellent! (1,003 reviews)
Breakfast was average. Breakfast is only included for two guest.

Reviewed on 13 Apr 2026

Holiday Inn & Suites Chicago - Downtown by IHG
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
354 North Union Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$353 per night from 26 Apr to 27 Apr
AU$353
26 Apr - 27 Apr
includes taxes & fees
9.2/10 Wonderful! (449 reviews)
Staff was unfriendly

Reviewed on 14 Apr 2026

Level Chicago Fulton Market
See all 4,818 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
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does a Near West Side holiday package cost?
Custom build your Near West Side package from a low AU$3,640. 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.