A train at a station with a cityscape in the background.

West Town Holidays from £797

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to £750 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

    Packages with flights are ATOL protected

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.

The Latest West Town Holiday Packages

Price found within the past 48 hours. Click for updated prices.
  • 20 Jan - 24 Jan

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

    Downtown Chicago
    4 nights
    4.0 star property
    9.4/10 - Exceptional (2,771 reviews)
    "Amazing view, but basic room"
    Reviewed November 7, 2026
    Return • London (LON) - Chicago (ORD)
    LHR - ORD • 1 stop ORD - LGW • 1 stop
    £1,019
    £797
    per traveller
    found 1 day ago
    Sable at Navy Pier Chicago, Curio Collection by Hilton
  • 20 Jan - 24 Jan

    Pendry Chicago + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.2/10 - Wonderful (1,162 reviews)
    "Beautiful rooms and service."
    Reviewed November 5, 2026
    Return • London (LON) - Chicago (ORD)
    LHR - ORD • 1 stop ORD - LGW • 1 stop
    £1,082
    £814
    per traveller
    found 1 day ago
    Pendry Chicago
  • 25 Dec - 30 Dec

    Trump International Hotel & Tower Chicago + Flight

    Downtown Chicago
    5 nights
    5.0 star property
    9.6/10 - Exceptional (2,077 reviews)
    "Beautiful hotel situated perfectly for most downtown Chicago activities. Attentive staff and amazing views from our 14th floor lake view room. This stay has been on my bucket list for awhile. This hotel experience did not disappoint"
    Reviewed November 6, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • Direct ORD - LHR • Direct
    £2,018
    £1,529
    per traveller
    found 1 day ago
    Trump International Hotel & Tower Chicago
  • 25 Dec - 30 Dec

    The Peninsula Chicago + Flight

    Downtown Chicago
    5 nights
    5.0 star property
    9.8/10 - Exceptional (1,008 reviews)
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • Direct ORD - LHR • Direct
    £2,673
    £2,123
    per traveller
    found 1 day ago
    The Peninsula Chicago
  • 25 Dec - 30 Dec

    Kimpton Gray Hotel by IHG + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    9.4/10 - Exceptional (1,004 reviews)
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • Direct ORD - LHR • Direct
    £1,348
    £1,075
    per traveller
    found 1 day ago
    Kimpton Gray Hotel by IHG

Where to stay in West Town

Find the best West Town areas for the activities you enjoy most.

Downtown Chicago

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Magnificent Mile

Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.

The Loop

Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.

River North

Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.

Lincoln Park

Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.

Discover the most popular places to visit in West Town

What to do near West Town

West Town Hotel Deals

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 travel package cost?

From as low as £797. 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.