West Town Vacation Packages

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Top Holiday Package Deals in West Town

Price found within the past 48 hours. Click for updated prices.
Millennium Knickerbocker Chicago

Millennium Knickerbocker Chicago

4 out of 5
Downtown Chicago
per person
Jul. 28 - Aug. 3
Roundtrip non-stop flight included
Ottawa (YOW) to Chicago (ORD)
7.8/10 Good! (1,743 reviews)
The staff is very friendly and helpful. This is my hotel of choice when I’m traveling to Chicago. Chiquita at the front desk is always helpful and very professional.

Reviewed on May 14, 2024

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 28 - Aug. 3
Roundtrip non-stop flight included
Ottawa (YOW) to Chicago (ORD)
8.6/10 Excellent! (189 reviews)
This hotel has a managing problem.

Reviewed on May 13, 2024

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 28 - Aug. 3
Roundtrip non-stop flight included
Ottawa (YOW) to Chicago (ORD)
8.8/10 Excellent! (207 reviews)
Thoroughly enjoyed my stay and my room. Will definitely book here again. Basic view of the courtyard but that was not important to me.

Reviewed on Mar. 16, 2024

Ambassador Chicago, part of JdV by Hyatt

Ambassador Chicago, part of JdV by Hyatt

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 28 - Aug. 3
Roundtrip non-stop flight included
Ottawa (YOW) to Chicago (ORD)
8.8/10 Excellent! (1,002 reviews)
Gorgeous neighborhood and close walk to lake and Michigan Avenue

Reviewed on May 16, 2024

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 28 - Aug. 3
Roundtrip non-stop flight included
Ottawa (YOW) to Chicago (ORD)
7.8/10 Good! (10 reviews)
Very nice stay, helpful staff.

Reviewed on Apr. 8, 2024

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 showing a city

Downtown Chicago

4 out of top 10 points of interest in this area

Known for its fascinating museums, stunning river views, and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Grant Park and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotel + flight trips in Downtown Chicago

West Town Hotel Deals

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 $202 per night from May 27 to May 28
CA $202
CA $238 total
includes taxes & fees
May 27 - May 28
7.6/10 Good! (6,732 reviews)
"A great and easy hotel to stay in for a short trip to Chicago! This location had everything you needed even an oven and microwave to use!"

Reviewed on May 13, 2024

Congress Plaza Hotel
Warwick Allerton - Chicago
Warwick Allerton - Chicago
4 out of 5
701 North Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $143 per night from May 27 to May 28
CA $143
CA $188 total
includes taxes & fees
May 27 - May 28
7.6/10 Good! (2,578 reviews)
"Very clean"

Reviewed on May 14, 2024

Warwick Allerton - Chicago
The Westin Michigan Avenue Chicago
The Westin Michigan Avenue Chicago
4.5 out of 5
909 North Michigan Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $208 per night from May 27 to May 28
CA $208
CA $279 total
includes taxes & fees
May 27 - May 28
8.6/10 Excellent! (1,000 reviews)
"We had a wonderful time in Chicago! This property was located in such a great area and easy walking to all the things we wanted to do...and eat. :)"

Reviewed on May 10, 2024

The Westin Michigan Avenue Chicago
See all 4,300 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.

Explore other types of vacation packages

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 $1,494, 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.

Discover the most popular places to visit in West Town

Image for Humboldt Park

Humboldt Park

Explore the great outdoors at Humboldt Park, a lovely green space in Chicago. Experience the acclaimed theater scene and entertainment choices in this vibrant area.

Humboldt Park
Image for Milwaukee Avenue

Milwaukee Avenue

You can enjoy retail therapy at Milwaukee Avenue during your visit to Chicago. Experience the live music and theater scene in this vibrant area.

Milwaukee Avenue
Image for The Salt Shed

The Salt Shed

You can get tickets for a performance at The Salt Shed during your stay in Chicago. Experience the live music and theater scene in this vibrant area.

The Salt Shed

Things to do

Image for Michelin Spanish Dinner with Live Flamenco

Michelin Spanish Dinner with Live Flamenco

CA $160
Per adult
Michelin Spanish Dinner with Live Flamenco
Image for Chicago Local Brewery Expedition with Homemade Guacamole

Chicago Local Brewery Expedition with Homemade Guacamole

CA $73
Per adult
Chicago Local Brewery Expedition with Homemade Guacamole
Image for Offbeat Street Art Tour of Chicago: Urban Graffiti, Art, and Murals

Offbeat Street Art Tour of Chicago: Urban Graffiti, Art, and Murals

CA $54
Per adult
100% of travellers recommend
Offbeat Street Art Tour of Chicago: Urban Graffiti, Art, and Murals
See all activities in Chicago

Other vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.