Lower West Side Holidays from £892

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Your Lower West Side Holiday

History, culture, food, fun — you'll find it all in Lower West Side. Discover the best of this neighbourhood with a holiday package to Lower West Side. Begin your trip to Lower West Side by heading to nearby attractions such as Willis Tower, University of Illinois Chicago and Skydeck Ledge. Whatever your dream Lower West Side holiday looks like, you can make it a reality with Expedia.

Price found within the past 48 hours. Click for updated prices.
The Wade

The Wade

4.5 out of 5
Downtown Chicago
Price was £1,163, price is now £892 per person
£892
per person
27 Apr - 2 May
found 3 hours ago
Return direct flight included
London (LGW) to Chicago (ORD)
8.4/10 Very Good! (1,444 reviews)
I had a great stay at the Wade Hotel in Chicago! The room was very clean and comfortable, and the staff was friendly, professional, and welcoming from check-in to check-out. The amenities were convenient, and the location made it easy to get around the city. I would definitely stay here again and recommend it to anyone visiting Chicago.

Reviewed on 9 Feb 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was £1,434, price is now £1,000 per person
£1,000
per person
27 Apr - 2 May
found 3 hours ago
Return direct flight included
London (LGW) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Everything and everyone was amazing definitely recommend

Reviewed on 10 Feb 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was £1,310, price is now £937 per person
£937
per person
27 Apr - 2 May
found 3 hours ago
Return direct flight included
London (LGW) to Chicago (ORD)
9.2/10 Wonderful! (347 reviews)
Hot tub wasn’t working(freezing cold) and no robes in my room. Need bigger roller carts and cheaper or free parking. Other than that the room, view, amenities were excellent.

Reviewed on 9 Feb 2026

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Price was £1,394, price is now £1,068 per person
£1,068
per person
27 Apr - 2 May
found 3 hours ago
Return direct flight included
London (LGW) to Chicago (ORD)
9.2/10 Wonderful! (1,404 reviews)
Great staff- very friendly

Reviewed on 9 Feb 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was £1,400, price is now £1,080 per person
£1,080
per person
21 Apr - 28 Apr
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
My girlfriend and I had an awesome time enjoying the space for a fun girls night out. Would recommend to anyone!

Reviewed on 2 Feb 2026

Where to stay in Lower West Side

Find the best Lower West Side areas and neighborhoods for the activities you enjoy most. Learn more about Lower West Side
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 Lower West Side

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 £77 per night from 12 Feb to 13 Feb
£77
12 Feb - 13 Feb
includes taxes & fees
8/10 Very Good! (9,876 reviews)
Staff was great, room service was quick and affordable. Room was spotless.

Reviewed on 10 Feb 2026

Congress Plaza Hotel
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is £168 per night from 7 Mar to 8 Mar
£168
7 Mar - 8 Mar
includes taxes & fees
8.2/10 Very Good! (2,211 reviews)
Easy booking, they let me check in early which I needed it. Friendly staff, nice bed, good shower pressure, clean room. Just need some updating to make it brighter room. Overall satisfied with my stay.

Reviewed on 2 Feb 2026

Hilton Chicago O'Hare Airport
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 £88 per night from 23 Feb to 24 Feb
£88
23 Feb - 24 Feb
includes taxes & fees
8.4/10 Very Good! (5,643 reviews)
Positives- As my friend said as we went to breakfast “the people here are so nice and look happy to work here!” I agree! Eloisa (I hope that is correct-our bartender ) made happy hour on Friday night even happier! She was friendly and knowledgeable, suggesting drinks we hadn’t had before just by ...

Reviewed on 8 Feb 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,854 properties in Lower West Side
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 Lower West Side travel package cost?
Handcraft your Lower West Side package from an affordable £892. Choose from any combination of hotels, flights and rental cars to craft the getaway you've been dreaming about for ages. Be sure to add on some activities and experiences!
If I'm not able to travel, can I cancel my Lower West Side travel package?
Yes, you can. We realise even the best-laid plans can fail, so we're here to help if you have to make changes to your Lower West Side travel package. You may be able to amend or cancel your itinerary for free if you've booked within 24 hours. Your airline, hotel or car rental company may charge you a fee if your booking was made more than 24 hours ago. Head to our Customer Service Portal for further information. Also, be sure to check your itinerary for the finer details on change fees.
How do I get a cheap travel package to Lower West Side?
One of the easiest ways to save dollars (and time) is to combine your bookings with Expedia. Hotels, flights, rental cars and activities — we've got them all covered. Choose the combination that best suits you and see your savings grow. We know a travel package is never a one-size-fits-all. That's why Expedia offers over 550 partner airlines and 1,000,000 hotel options worldwide, which lets you customize your Lower West Side getaway.
Does Expedia offer Book Now, Pay Later Lower West Side holidays?
We do. Expedia has partnered with online lender Klarna to help you conveniently pay for your trip in manageable instalments. Simply click on the payment plan best suited to your needs during the checkout process and take away the stress of budgeting for your next trip. Remember to bundle your accommodation, flights and car hire with Expedia to get the biggest bang for your buck. Check out our flexible payment options below:

  • Pay monthly holidays: Klarna has convenient monthly payment plans that work for all types of budgets, so you can have that well-deserved holiday now.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna makes it easy to pay off your trip in multiple transactions.
  • Low deposit holidays: When you want to jump on an awesome deal but don't have the full amount yet, Klarna's low deposit holiday plan will help you lock it in.

Where should I stay in Lower West Side?
Take the leg work out of sightseeing by staying in a hotel just a stone's throw away from Lower West Side's terrific attractions. Millennium Park and Wrigley Field are two of the best in this neighbourhood.
What are the top hotels in Lower West Side?
Hyatt Regency Chicago and The Godfrey Hotel Chicago are a couple of the most popular properties in Lower West Side. Why not check out the rates and amenities at each and then make up your mind?
How far in advance should I book my Lower West Side holiday?
It can be tricky to know when is the ideal time to book your Lower West Side trip. But generally the earlier you book, the more affordable the prices. Sometimes, you can book your flights and hotels nearly 12 months prior to departure. If you're eager to escape on a last-minute getaway, no need to panic! There are plenty of fantastic bargains advertised on Expedia every single day.
What does an Expedia Lower West Side travel package include?
Much of that depends on you. You can pick from a variety of Lower West Side packages, such as a rental car, flight and hotel. You can also book a hotel with a flight, or a rental car with a flight. Once you've made your booking, you can add the fun stuff like activities and experiences. Whatever your Lower West Side trip looks like, get ready to save!
What should I know before booking a Lower West Side travel package?
Find deals that match your budget with an Expedia package. Hotels, flights, rental cars — we have everything you need to plan your break. You'll save big bucks just by bundling your bookings. Whether you're going on a ski trip or drinking cocktails on a beach, your dream getaway is only clicks away.
Can I choose my airline with a Lower West Side Expedia travel package?
You can, and with over 550 airlines to select from across the globe, you have loads of choice. Browse the available options and find out which airline suits your needs and budget.

Things to do

Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

£18
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Flyover in Chicago

Flyover in Chicago

£28
per adult
98% of travellers recommend
Flyover in Chicago
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
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.