West Town Holidays from £894

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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 Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,455, price is now £894 per person
£894
per person
3 Oct - 10 Oct
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (2,028 reviews)
Close to walk most places. Lots of restaurants in the surrounding area. Staff very nice. Rooms clean and spacious.

Reviewed on 22 Aug 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,643, price is now £1,044 per person
£1,044
per person
3 Oct - 10 Oct
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (666 reviews)
Hotel is located very centric. Nice view very quiet

Reviewed on 22 Aug 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,626, price is now £1,095 per person
£1,095
per person
3 Oct - 10 Oct
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (277 reviews)
The staff were excellent

Reviewed on 21 Aug 2025

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,519, price is now £1,034 per person
£1,034
per person
3 Oct - 10 Oct
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,825 reviews)
Staying here was nothing short of amazing thanks to this staff. They were very friendly, courteous and nice. Everyone was attentive and you can tell. They really loved working there and delivering service.

Reviewed on 20 Aug 2025

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,636, price is now £1,118 per person
£1,118
per person
3 Oct - 10 Oct
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,336 reviews)
No hot water in the shower for the entirety of our 3 night stay, it was barely warm. Complained multiple times, other guests were also facing the same problem. The responses ranged from "engineers are working on it" to "leave the water running for longer" to finally "that is the hottest water you're going to get". That was unbelievable given that the sink had hotter water than the shower. Upon my insistence, they offered to move us to a different room the next day after 3pm - that meant we would have had to take cold showers for 2 days. In the end we just didn't take up the moving-rooms hassle in the middle of our trip.

Reviewed on 18 Aug 2025

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

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

The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £131 per night from 2 Sept to 3 Sept
£131
2 Sept - 3 Sept
includes taxes & fees
8.2/10 Very Good! (1,210 reviews)
"The room and view were super nice. Even with not being on the waterfront side of the build we werent disappointed. Check in staff could be nicer but the bar staff was excellent. Nice and informative for travelers. The pier was i. Walking distance. Food and shopping all around and spotless insude ..."

Reviewed on 20 Aug 2025

The Wade
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 £165 per night from 14 Sept to 15 Sept
£165
14 Sept - 15 Sept
includes taxes & fees
7.8/10 Good! (9,014 reviews)
"Great hotel"

Reviewed on 20 Aug 2025

Congress Plaza Hotel
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £132 per night from 3 Sept to 4 Sept
£132
3 Sept - 4 Sept
includes taxes & fees
8.4/10 Very Good! (4,726 reviews)
"Valet parking was very expensive for leaving your car without using it for 2 days."

Reviewed on 20 Aug 2025

Embassy Suites by Hilton Chicago Downtown River North
See all 4,758 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 £894. 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

CHICAGo MUSt Do Hidden GEm SPEAKeasy's

CHICAGo MUSt Do Hidden GEm SPEAKeasy's

£38
per adult
CHICAGo MUSt Do Hidden GEm SPEAKeasy's
Chicago: Tapas & Flamenco Dinner in Ukrainian Village

Chicago: Tapas & Flamenco Dinner in Ukrainian Village

£125
per adult
Chicago: Tapas & Flamenco Dinner in Ukrainian Village
Offbeat Street Art Tour of Chicago: Urban Graffiti, Art, and Murals

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

£30
per adult
100% of travellers recommend
Offbeat Street Art Tour of Chicago: Urban Graffiti, Art, and Murals
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.