West Town Holidays from £1,547

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Your West Town Holiday

Make travel planning easier by booking a holiday package to West Town. We'll take care of all the details, so you can focus on soaking up everything this neighbourhood has to offer. Kick off your trip to West Town with a visit to nearby attractions such as Millennium Park, Willis Tower and John Hancock Centre. Don't just wish for it — make it a reality! Lock in your perfect West Town holiday with Expedia and get to where you're going your way.

Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was £1,888, price is now £1,547 per person
£1,547
per person
30 Jul - 3 Aug
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (120 reviews)
The hotel is fresh and clean. Very nice facility. Staff anre wonderful. Only comment is there should be free water in the rooms, at least for Marriott members. For the rates charged, water should be included. Water pressure is a bit low.

Reviewed on 21 Jun 2026

Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Downtown Chicago
Price was £2,134, price is now £1,673 per person
£1,673
per person
10 Sept - 16 Sept
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,248 reviews)
My fave Chicago stay

Reviewed on 19 Jun 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was £2,469, price is now £1,948 per person
£1,948
per person
30 Jul - 3 Aug
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (1,893 reviews)
hotel was immaculate and the people were amazing.

Reviewed on 20 Jun 2026

Hotel Chicago Downtown, Autograph Collection by Marriott

Hotel Chicago Downtown, Autograph Collection by Marriott

4 out of 5
Downtown Chicago
Price was £1,938, price is now £1,562 per person
£1,562
per person
10 Sept - 16 Sept
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,003 reviews)
Facility was nice. Resort fee was lame cuz couldn’t use it for coffee. 2 of 3 staff I interacted with were unfriendly, and unhelpful. 1 of 3 was great.

Reviewed on 22 Jun 2026

Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Downtown Chicago
Price was £2,049, price is now £1,665 per person
£1,665
per person
30 Jul - 3 Aug
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,399 reviews)
I truly enjoyed my stay at this hotel. From the moment I arrived, the staff made me feel welcome and valued. Everyone was so friendly, attentive, and genuinely eager to help, which made the experience even more enjoyable. The hotel was clean, comfortable, and had everything I needed for a relaxing stay. I especially loved the location—it was convenient to restaurants, shopping, and local attractions, making it easy to get around and enjoy the area without any hassle.

Reviewed on 21 Jun 2026

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

Top hotels in West Town

STAY

STAY

2 out of 5
1415 Ashland Ave Chicago IL
The price is £79 per night from 6 Jul to 7 Jul
£79
6 Jul - 7 Jul
includes taxes & fees
7.6/10 Good! (232 reviews)
"Room was dirty, shower grout featured black mold, the first room they tried to put me in smelled horrible they had to put me in another room which was really dirty. Just spend the extra dollars and stay at an actual hotel. When approached about the cleanliness they tried to gaslight me that "they ..."

Reviewed on 20 Jun 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 £123 per night from 29 Jun to 30 Jun
£123
29 Jun - 30 Jun
includes taxes & fees
8/10 Very Good! (10,167 reviews)
"Room smelled a little like mold or sitting water although the floors were never and the room was clear overall. The shower had a lot of rust in it. Hotel does not offer parking and the garage they recommend is was already full."

Reviewed on 23 Jun 2026

Congress Plaza Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is £125 per night from 7 Jul to 8 Jul
£125
7 Jul - 8 Jul
includes taxes & fees
9/10 Wonderful! (4,465 reviews)
"Great location, rooms and service"

Reviewed on 23 Jun 2026

Hilton Chicago/Magnificent Mile Suites
See all 4,808 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
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a West Town travel package cost?
From as low as £1,547. Yes, you read that right. Our West Town travel packages are a simple way to make your budget last longer. Combine your flights, hotels and rental car and explore this fabulous destination.
If I'm not able to travel, can I cancel my West Town travel package?
Whether it's your hotel, flight or rental car, you can cancel and rebook it. Locked in your West Town travel package in the last 24 hours? You may be able to make any changes for free. For older bookings, you may be charged a fee by your airline, hotel or car rental company. For more details, take a look at our Customer Service Portal. We'll help you each step of the way.
How do I get a cheap travel package to West Town?
If you love amazing deals, combine your bookings into a West Town travel package. Whether you need hotels, flights, activities or rental cars, you can book everything in one place. You'll have lots of choice at your fingertips too. Expedia has more than 550 airlines and 1,000,000 hotels throughout the world to choose from. Fly with who you want, check in where you like and save precious money — now that's the perfect holiday!
Does Expedia offer Book Now, Pay Later West Town holidays?
Your bank balance shouldn't stop you from taking a holiday, so Expedia has worked out a solution to help. Now that we've teamed up with online lender Klarna, it's easier than ever to book an incredible getaway without using up all your savings. Klarna offers flexible payment options during the checkout process that take the stress out of budgeting for your break. Check out these flexible payment options:

  • Pay monthly holidays: Klarna has convenient monthly payment plans that work for all budgets, so you can escape on that well-earned holiday now.
  • Pay in instalments holidays: If you want to pay off your getaway in multiple transactions, holidays paid in instalments might be the right option for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: If paying a small percentage of your trip (rather than all of it upfront) makes it easier to hit that "book now" button, consider a low deposit holiday payment plan with Klarna.

Where should I stay in West Town?
Make sightseeing easy by staying someplace close to West Town's fantastic attractions. Millennium Park and Wrigley Field are two which top many visitors' bucket lists.
What are the top hotels in West Town?
If it's your first time in West Town, secure a room at Hyatt Regency Chicago or The Godfrey Hotel Chicago. Both hotels will make you feel at home and are favourites among many travellers.
How far in advance should I book my West Town holiday?
Travellers can normally compare international fares on Expedia up to a year in advance of departure. Booking late? With a little bit 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?
You can choose from any combination of rental cars, hotels and flights. Once you've made your booking, you can add the fun stuff like experiences and tours. Want to pick your airfare class? That's also possible. The choice is yours when it comes to creating your dream West Town trip.
What should I know before booking a West Town travel package?
You can look forward to saving with an Expedia travel package. Combine your flights, rental cars and hotels and score fantastic discounts. You're not limited to hotels, however. Book with us and choose from oceanfront condos, cabins in the mountains and even ranches and treehouses!
Can I choose my airline with a West Town Expedia travel package?
Yes — that's the beauty of an Expedia package. You get to choose. We have access to more than 550 partner airlines around the world, so you have options galore when putting together your West Town getaway.

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£18
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£30
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Chicago C3® : Save on admission to your choice of 3 top attractactions

Chicago C3® by CityPASS®

£81
per adult
88% of travellers recommend
Chicago C3® by CityPASS®
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. Flight-inclusive packages are ATOL protected.