West Town Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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

Top Holiday Package Deals in West Town

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was CA $1,492, price is now CA $1,028 per person
CA $1,028
per person
Oct 23 - Oct 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (4,770 reviews)
Excellent Staff,nice location,I'm would come again..

Reviewed on Jul 27, 2026

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
Downtown Chicago
Price was CA $7,890, price is now CA $4,967 per person
CA $4,967
per person
Sep 27 - Oct 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,002 reviews)

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $2,883, price is now CA $1,820 per person
CA $1,820
per person
Sep 27 - Oct 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (533 reviews)

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was CA $2,127, price is now CA $1,441 per person
CA $1,441
per person
Sep 27 - Oct 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,606 reviews)
I'll choose another hotel next month.

Reviewed on Jul 27, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $1,921, price is now CA $1,352 per person
CA $1,352
per person
Sep 12 - Sep 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (504 reviews)

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
A busy city street with tall buildings, a bus, and cars.

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

West Town Hotel Deals

STAY

STAY

2 out of 5
1415 Ashland Ave Chicago IL
The price is CA $54 per night from Jul 28 to Jul 29
CA $54
CA $140 total
Jul 28 - Jul 29
includes taxes & fees
7.6/10 Good! (243 reviews)
"Room needed some work done like the outlet table did not work. The patio was under construction which I would have appreciated a heads up on since that was a major reason I chose to book. Other than that it was comfy."

Reviewed on Jul 24, 2026

STAY
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 CA $234 per night from Aug 10 to Aug 11
CA $234
CA $279 total
Aug 10 - Aug 11
includes taxes & fees
Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $245 per night from Aug 9 to Aug 10
CA $245
CA $291 total
Aug 9 - Aug 10
includes taxes & fees
8.2/10 Very good! (1,856 reviews)
"Staff were excellent. Hotel was kind of dingy. Breakfast outrageously expensive."

Reviewed on Jul 26, 2026

The Chicago Hotel Collection Ambassador Gold Coast
See all 4,623 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 Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a West Town vacation package cost?
Starting from as low as CA $1,028, 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 vacation 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 Center 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 travelers.
How far in advance should I book my West Town vacation?
Travelers 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 favorite 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 vacation.
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 organizing 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 vacation 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 vacation.
If I'm not able to travel, can I cancel my West Town vacation package?
Whether it's your flight or hotel, yes, you can amend or cancel it. Locked in your West Town vacation 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.

Stay near popular West Town attractions

A riverside path with a stone edge, lush greenery, and yellow flowers.

Humboldt Park

7.0/10 (2 reviews)
Humboldt Park is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Experience the acclaimed art scene and entertainment choices in this vibrant area.
See properties

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $31
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

CA $35
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's Lake and River Architecture Tour

Wendella's Lake and River Architecture Tour

CA $64
per adult
94% of travellers recommend
Wendella's Lake and River Architecture Tour
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.