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
Price found within the past 48 hours. Click for updated prices.
  • Bar (on property)
    Aug 11 - Aug 15

    The Whitehall Hotel, BW Premier Collection + Flight

    Downtown Chicago
    4 nights
    3.5 star property
    8.4/10 - Very good (3,928 reviews)
    "Overall a great stay, staff was friendly and bed was comfy."
    Reviewed June 6, 2026
    Roundtrip • Montreal (YUL) - Chicago (ORD)
    YUL - ORD • Nonstop ORD - YUL • Nonstop
    CA $1,258
    CA $947
    per traveller
    found 1 day ago
    The Whitehall Hotel, BW Premier Collection
  • Terrace/patio
    Aug 11 - Aug 15

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

    Downtown Chicago
    4 nights
    4.0 star property
    9.4/10 - Exceptional (2,526 reviews)
    "Loved the location. Fitness room was a little disappointing because it’s small and the there are only 2 peloton bikes, but one was out of commission."
    Reviewed June 4, 2026
    Roundtrip • Montreal (YUL) - Chicago (ORD)
    YUL - ORD • Nonstop ORD - YUL • Nonstop
    CA $1,852
    CA $1,331
    per traveller
    found 1 day ago
    Sable at Navy Pier Chicago, Curio Collection by Hilton
  • Full-size fridge, microwave, oven, stovetop
    Aug 7 - Aug 10

    Level Chicago – Old Town + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    9.0/10 - Wonderful (488 reviews)
    "Very clean and loved the location and amenities with the store on the first floor was fantastic"
    Reviewed June 3, 2026
    Roundtrip • Toronto (YTZ) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YTZ • Nonstop
    CA $1,876
    CA $1,378
    per traveller
    found 1 day ago
    Level Chicago – Old Town
  • Lounge
    Jul 23 - Jul 26

    Pendry Chicago + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.2/10 - Wonderful (1,122 reviews)
    "I absolutely loved it! I little bit noisy but close to literally everything!"
    Reviewed June 2, 2026
    Roundtrip • Montreal (YUL) - Chicago (MDW)
    YUL - MDW • 1 stop MDW - YUL • 1 stop
    CA $2,295
    CA $1,689
    per traveller
    found 2 days ago
    Pendry Chicago
  • Breakfast and dinner served
    Aug 11 - Aug 15

    Omni Chicago Hotel + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.2/10 - Wonderful (1,792 reviews)
    "Booked a room - got a suite! Enjoyed the extra space. A separate living room for watching TV or working at a desk. Staff at the hotel was very helpful. Enjoyed the breakfast too."
    Reviewed June 3, 2026
    Roundtrip • Montreal (YUL) - Chicago (ORD)
    YUL - ORD • Nonstop ORD - YUL • Nonstop
    CA $1,332
    CA $986
    per traveller
    found 1 day ago
    Omni Chicago Hotel

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

West Town Hotel Deals

STAY

STAY

2 out of 5
1415 Ashland Ave Chicago IL
The price is CA $65 per night from Jul 6 to Jul 7
CA $65
CA $153 total
Jul 6 - Jul 7
includes taxes & fees
7.8/10 Good! (221 reviews)
"Awesome staff response"

Reviewed on Jun 5, 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 $202 per night from Jun 29 to Jun 30
CA $202
CA $241 total
Jun 29 - Jun 30
includes taxes & fees
8/10 Very Good! (10,192 reviews)
"ok"

Reviewed on Jun 7, 2026

Congress Plaza Hotel
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundable
The price is CA $212 per night from Jun 28 to Jun 29
CA $212
CA $252 total
Jun 28 - Jun 29
includes taxes & fees
7.8/10 Good! (1,530 reviews)
"There isn't a coffee machine in the room one is supposed to be in the lobby but although the machines there were 4 there wasn't any tea or coffee pods."

Reviewed on Jun 7, 2026

The Chicago Hotel Collection - Magnificent Mile
See all 4,764 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
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Beach Vacations
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Frequently asked questions

How much does a West Town vacation 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 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.

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $37
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Wendella's Lake and River Architecture Tour

Wendella's Lake and River Architecture Tour

CA $62
per adult
94% of travellers recommend
Wendella's Lake and River Architecture Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $55
per adult
94% of travellers recommend
Wendella's 90-min Chicago 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.