West Town Holidays

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Your West Town Holiday

West Town is beckoning! Whatever type of getaway you have in mind, you can experience and see more of this neighbourhood with a West Town holiday package. Your trip to West Town wouldn't be complete without a stop at major attractions nearby such as University of Illinois Chicago, United Centre and Anna and Frederick Douglass Park. Don't just think about it — turn it into a reality! Lock in your ultimate West Town holiday with Expedia and experience travel your way.

Price found within the past 48 hours. Click for updated prices.
  • Meeting facility
    Jul 28 - Aug 4

    Thompson Chicago, by Hyatt + Flight

    Downtown Chicago
    7 nights
    4.5 star property
    9.2/10 - Wonderful (1,370 reviews)
    "Excellent hotel and close to restaurants and shopping. Very clean."
    Reviewed May 24, 2026
    Return • Sydney (SYD) - Chicago (ORD)
    SYD - ORD • 1 stop ORD - SYD • 1 stop
    AU$4,948
    AU$3,786
    per traveller
    found 1 day ago
    Thompson Chicago, by Hyatt
  • Indoor wedding
    Jul 28 - Aug 4

    Swissotel - Chicago + Flight

    Downtown Chicago
    7 nights
    4.5 star property
    9.0/10 - Wonderful (3,348 reviews)
    "Excellent location, walk to all major attractions. Friendly staff. Hotel room was very clean and comfortable. Price was pretty reasonable"
    Reviewed May 26, 2026
    Return • Sydney (SYD) - Chicago (ORD)
    SYD - ORD • 1 stop ORD - SYD • 1 stop
    Save 100% on your flight
    AU$6,123
    AU$3,882
    per traveller
    found 1 day ago
    Swissotel - Chicago
  • Terrace/patio
    Jul 28 - Aug 4

    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)
    "Great views of the lake, staff very helpful the rooms were clean and comfortable. Would stay there again!"
    Reviewed May 26, 2026
    Return • Sydney (SYD) - Chicago (ORD)
    SYD - ORD • 1 stop ORD - SYD • 1 stop
    AU$5,762
    AU$4,025
    per traveller
    found 1 day ago
    Sable at Navy Pier Chicago, Curio Collection by Hilton
  • 2 restaurants; breakfast, lunch, and dinner served
    Jul 28 - Aug 4

    LondonHouse Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    7 nights
    4.5 star property
    9.4/10 - Exceptional (3,727 reviews)
    "Excellent location! Great views from our room."
    Reviewed May 25, 2026
    Return • Sydney (SYD) - Chicago (ORD)
    SYD - ORD • 1 stop ORD - SYD • 1 stop
    AU$6,045
    AU$4,257
    per traveller
    found 1 day ago
    LondonHouse Chicago, Curio Collection by Hilton
  • Executive lounge
    Jul 28 - Aug 4

    Fairmont Chicago at Millennium Park + Flight

    Downtown Chicago
    7 nights
    4.5 star property
    8.8/10 - Excellent (2,170 reviews)
    "Amazing view and clean room"
    Reviewed May 25, 2026
    Return • Sydney (SYD) - Chicago (ORD)
    SYD - ORD • 1 stop ORD - SYD • 1 stop
    AU$5,126
    AU$3,886
    per traveller
    found 1 day ago
    Fairmont Chicago at Millennium Park

Our guide on where to stay in West Town

Find the best West Town areas and neighborhoods for the activities you enjoy most. Learn more about West Town
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 West Town Hotel Deals

STAY

STAY

2 out of 5
1415 Ashland Ave Chicago IL
The price is AU$139 per night from 2 June to 3 June
AU$139
2 June - 3 June
includes taxes & fees
7.8/10 Good! (216 reviews)
"Very dirty, roaches, mice, bad part of town. Be very careful."

Reviewed on 25 May 2026

STAY
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
The price is AU$224 per night from 27 May to 28 May
AU$224
27 May - 28 May
includes taxes & fees
8/10 Very Good! (10,141 reviews)
"Everything was perfect. Great customer service."

Reviewed on 25 May 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
The price is AU$337 per night from 27 May to 28 May
AU$337
27 May - 28 May
includes taxes & fees
9.4/10 Exceptional! (4,252 reviews)
"This hotel is amazing, Great location, super clean and stuff was kind, informative and very respectful! The breakfast was well organized considering the amount people served! Not a missing items at any moment! The rooftop bar was very pleasant place to sit and chill. Strongly recommended!!!"

Reviewed on 26 May 2026

Hotel Riu Plaza Chicago
See all 4,780 properties in West Town
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 West Town holiday package cost?
Starting from as low as , you can customize your West Town package the way you want. Simply bundle hotels, flights and car rentals and we'll reward you with discounts.
How do I get a cheap travel package to West Town?
Just think of all the thrilling things you could do in West Town with extra cash in your wallet. Watch your savings stack up when you combine your hotel and airfare bookings into a West Town holiday package. You have plenty of choice with Expedia too. In fact, you can choose from more than 550 air carriers and 1 000 000 hotel options worldwide. Whether you're taking off with the entire family or adventuring alone, exploring West Town is better with a package.
Where should I stay in West Town?
Visitors come from every corner of the globe to experience University of Illinois Chicago and United Centre in West Town. Book a room close to these fantastic attractions to make sightseeing a breeze.
What are the top hotels in West Town?
If this will be your first time in West Town, book a room at Hyatt Place Chicago/Wicker Park or House Of Two Urns B&B. Both offer comfy beds and are popular options with many savvy travellers.
How far in advance should I book my West Town holiday?
Travellers can normally look up international fares on Expedia within 12 months of departure. Booking at the last minute? With a stroke of luck, it's still possible to nab a cheap ticket just weeks before your flight.
What does an Expedia West Town travel package include?
Hotels, car rentals and flights — we connect you to all the best deals. All you'll have to do is pick your favourite combination. After you've made your booking, you can add on the fun stuff like activities and sightseeing tours. Our travel packages make it easy to customize an amazing West Town holiday.
What should I know before booking a West Town travel package?
You'll pick up terrific savings when you bundle your flights, hotels and rental cars into a travel package. Plus, booking everything in one place will make your trip planning easier. So why waste your time or money? Whether you're organising a luxury romantic escape or a budget family adventure, have a look at our package deals today.
Can I choose my airline with a West Town Expedia holiday package?
Expedia has access to more than 550 airline partners worldwide, so you definitely can. Simply pick your preferred air carrier and put together your ideal West Town holiday.
If I'm not able to travel, can I cancel my West Town holiday package?
Whether it's your flight or hotel, yes, you can amend or cancel it. Locked in your West Town holiday package in the last 24 hours? You may be able to make changes for free. For bookings older than that, you may incur a charge from your hotel, airline or car rental company. For further information, take a look at our Customer Service Portal. We'll help you each step of the way.

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.