Near West Side Holidays

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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.

Price found within the past 48 hours. Click for updated prices.
  • Smart TV
    Jul 10 - Jul 17

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    7 nights
    4.0 star property
    9.2/10 - Wonderful (490 reviews)
    "Amazing place"
    Reviewed May 26, 2026
    Return • Melbourne (MEL) - Chicago (ORD)
    MEL - ORD • 1 stop ORD - MEL • 1 stop
    AU$4,642
    AU$3,264
    per traveller
    found 1 day ago
    Level Chicago Fulton Market
  • Terrace/patio
    Jul 10 - Jul 17

    Trump International Hotel & Tower Chicago + Flight

    Downtown Chicago
    7 nights
    5.0 star property
    9.6/10 - Exceptional (1,886 reviews)
    "I really can’t say any thing negative. It was one of the cleanest hotel I ever stayed. Super nice staff.and location was excellent."
    Reviewed May 30, 2026
    Return • Melbourne (MEL) - Chicago (ORD)
    MEL - ORD • 1 stop ORD - MEL • 1 stop
    AU$6,049
    AU$4,393
    per traveller
    found 1 day ago
    Trump International Hotel & Tower Chicago
  • 2 restaurants; breakfast, lunch and dinner served
    Jul 10 - Jul 17

    LondonHouse Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    7 nights
    4.5 star property
    9.4/10 - Exceptional (3,724 reviews)
    "Extraordinarily lovely and helpful staff. This hotel manages to promote a staff and facility that beautifully balance solid upscale services with a true sence of welcome and connection, with a warm but unintrusive vibe and clear consideration of it's guests."
    Reviewed May 31, 2026
    Return • Melbourne (MEL) - Chicago (ORD)
    MEL - ORD • 1 stop ORD - MEL • 1 stop
    AU$5,196
    AU$3,776
    per traveller
    found 1 day ago
    LondonHouse Chicago, Curio Collection by Hilton
  • Terrace/patio
    Jul 10 - Jul 17

    Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    7 nights
    4.0 star property
    9.4/10 - Exceptional (2,515 reviews)
    "Without a doubt, the view of the pier and city skyline was the BEST part of this hotel experience. The room was pretty large and had a great sitting area to read, gaze at the water, people watch, and relax. The hotel staff was nice and helpful. Everything I needed and wanted to do for this trip was at the Navy Pier so the Sable Hotel checked all my boxes."
    Reviewed May 28, 2026
    Return • Melbourne (MEL) - Chicago (ORD)
    MEL - ORD • 1 stop ORD - MEL • 1 stop
    AU$4,869
    AU$3,599
    per traveller
    found 1 day ago
    Sable at Navy Pier Chicago, Curio Collection by Hilton
  • Indoor wedding
    Jul 10 - Jul 17

    Swissotel - Chicago + Flight

    Downtown Chicago
    7 nights
    4.5 star property
    9.0/10 - Wonderful (3,359 reviews)
    "Staff was so helpful"
    Reviewed May 29, 2026
    Return • Melbourne (MEL) - Chicago (ORD)
    MEL - ORD • 1 stop ORD - MEL • 1 stop
    AU$5,209
    AU$3,856
    per traveller
    found 1 day ago
    Swissotel - Chicago

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$313 per night from 29 June to 30 June
AU$313
29 June - 30 June
includes taxes & fees
9/10 Wonderful! (2,228 reviews)
"N/a"

Reviewed on 30 May 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$296 per night from 1 July to 2 July
AU$296
1 July - 2 July
includes taxes & fees
8.6/10 Excellent! (1,009 reviews)
"great place. located nearby usefully metro. some nearby areas a little rundown"

Reviewed on 30 May 2026

Holiday Inn & Suites Chicago - Downtown by IHG
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 AU$231 per night from 29 June to 30 June
AU$231
29 June - 30 June
includes taxes & fees
8/10 Very Good! (10,136 reviews)
"Bath tub didn’t drain, elevator/s didn’t work, we could hear the people next door like there weren’t even walls in between us."

Reviewed on 31 May 2026

Congress Plaza Hotel
See all 4,764 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
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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 . 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

Aerial view of the iconic John Hancock Center and shimmering skyscrapers meeting the tranquil blue of Lake Michigan's shoreline, Chicago, Illinois, United States.

United Center

5/5(9 reviews)

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
Tri Taylor

University of Illinois Chicago

4.5/5(5 reviews)

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

University of Illinois Chicago

Activities

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

AU$37
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

AU$61
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Art Institute of Chicago

Art Institute of Chicago

AU$55
per adult
92% of travellers recommend
Art Institute of Chicago
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.