West Town Holidays from £1,203

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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.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was £1,740, price is now £1,203 per person
£1,203
per person
17 Jun - 22 Jun
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (3,293 reviews)
Having stayed in the lovely Swissotel Bosphorus/Istanbul, I was hesitant to compare Swissotel experience & hope Chicago would be as good. No. Not even close. The elevated Swissotel brand is not represented here well in this building at all. The valet is $87! Self park is $70 and the self park area doesn’t even have an elevator up to the lobby, you have to walk through a dark, confusing, and claustrophobic garage to stairs then to elevator. Staff were tactful & kind, it’s just the building is old, needs renovation, & the room air is stuffy. A positive bright light was the stunning view from the gym and the lobby ambience & smell.

Reviewed on 6 May 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £3,001, price is now £2,166 per person
£2,166
per person
8 Jun - 14 Jun
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,851 reviews)
I love everything in the hotel everything

Reviewed on 4 May 2026

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 £2,230, price is now £1,613 per person
£1,613
per person
19 Jul - 26 Jul
found 19 hours ago
Return direct flight included
Glasgow (GLA) to Chicago (ORD)
9.4/10 Exceptional! (2,478 reviews)
Thank you to Javon who was super helpful in our check in . The staff was so nice and accommodating. Additional linens were delivered in less than 5 minutes and then even extended our check out to 1pm. I will definitely be back when I’m in Chicago to try to catch fireworks. Our corner room was outstanding and breathtaking

Reviewed on 3 May 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was £2,389, price is now £1,738 per person
£1,738
per person
8 Jun - 14 Jun
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (3,670 reviews)
Amazing hotel and staff!

Reviewed on 5 May 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was £2,352, price is now £1,741 per person
£1,741
per person
19 Jul - 26 Jul
found 19 hours ago
Return direct flight included
Glasgow (GLA) to Chicago (ORD)
8.8/10 Excellent! (2,137 reviews)
Keep an eye that nothing is added from the minibar but great property and can't wait to stay again!

Reviewed on 5 May 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

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

Top hotels in West Town

STAY

STAY

2 out of 5
1415 Ashland Ave Chicago IL
The price is £69 per night from 19 May to 20 May
£69
19 May - 20 May
includes taxes & fees
7.8/10 Good! (206 reviews)
microwave was not functioning, Bed was old and making lot of noise and disturbance to sleep. Bathroom is tooooooo small.

Reviewed on 19 Apr 2026

STAY
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
The price is £99 per night from 25 May to 26 May
£99
25 May - 26 May
includes taxes & fees
8.2/10 Very Good! (2,683 reviews)
Friendly staff. Good location

Reviewed on 5 May 2026

Hotel Felix River North/Magnificent Mile
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
The price is £119 per night from 26 May to 27 May
£119
26 May - 27 May
includes taxes & fees
8.8/10 Excellent! (5,167 reviews)
This hotel is conveniently located on the Riverwalk, which makes it accessible to so much. Our room was a little on the small side and the air-conditioning did not work. The staff was friendly and it’s a great location to catch an Uber.

Reviewed on 6 May 2026

River Hotel
See all 4,783 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 £1,203. 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

£20
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

£32
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Art Institute of Chicago

Art Institute of Chicago

£29
per adult
94% of travellers recommend
Art Institute of Chicago
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.