West Town Holidays

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

Congress Plaza Hotel

3.5 out of 5
Downtown Chicago
per person
23 Dec - 30 Dec
found 21 hours ago
Return direct flight included
Milan (MXP) to Chicago (ORD)
7.8/10 Good! (7,993 reviews)
I thought the staff was really helpful. I wasn’t a fan of the parking situation but the garage next door was nice to deal with. They just kept calling with stipulations like you can’t come and go with the car easily and because of concerts we wouldn’t have access at times, that kind of thing. It was convenient for transportation, walking, food and other conveniences which was nice. The room was really nice but the air conditioning/heat kept getting stuck on high blast and was too warm for our liking even when we tried to adjust it, made for difficult sleeping. Price was good and fair compared to other sites in the area.

Reviewed on 20 Nov,2024

Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
Downtown Chicago
per person
23 Dec - 30 Dec
found 21 hours ago
Return direct flight included
Milan (MXP) to Chicago (ORD)
8.2/10 Very Good! (2,454 reviews)
Stay was great, hated parking fees

Reviewed on 20 Nov,2024

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
Downtown Chicago
per person
23 Dec - 30 Dec
found 21 hours ago
Return direct flight included
Milan (MXP) to Chicago (ORD)
8.8/10 Excellent! (1,730 reviews)
Staff was excellent, room is comfortable

Reviewed on 17 Nov,2024

Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
Unlock Black Friday deals

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 featuring a city

Downtown Chicago

5 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 Michigan Avenue and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotels in Downtown Chicago

Top hotels in West Town

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 S$134 per night from 25 Nov to 26 Nov
S$134
includes taxes & fees
25 Nov - 26 Nov
7.8/10 Good! (8,136 reviews)
"Great staff made the stay worth it. Will go back when I return to Chicago."

Reviewed on 19 Nov,2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$165 per night from 22 Dec to 23 Dec
S$165
includes taxes & fees
22 Dec - 23 Dec
8.6/10 Excellent! (3,542 reviews)
"Highly recommend ."

Reviewed on 20 Nov,2024

River Hotel
Club Quarters Hotel, Central Loop, Chicago
Club Quarters Hotel, Central Loop, Chicago
4 out of 5
111 West Adams Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$151 per night from 22 Dec to 23 Dec
S$151
includes taxes & fees
22 Dec - 23 Dec
8.4/10 Very Good! (3,270 reviews)
"Great place"

Reviewed on 19 Nov,2024

Club Quarters Hotel, Central Loop, Chicago
See all 4,211 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.

Frequently asked questions

How much does a West Town holiday package cost?
Starting from as low as S$1,648, 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.

Things to do

Shooting + Spinning Private Art Experience

Shooting + Spinning Private Art Experience

S$122
Per adult
Shooting + Spinning Private Art Experience
Chicago: Tapas & Flamenco Dinner in Ukrainian Village

Chicago: Tapas & Flamenco Dinner in Ukrainian Village

S$247
Per adult
Chicago: Tapas & Flamenco Dinner in Ukrainian Village
Romantic Date Private Art Experience

Romantic Date Private Art Experience

S$601
Per adult
Romantic Date Private Art Experience
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.