Lower West Side Holidays from £902

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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.
Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination

Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination

3.5 out of 5
Price was £1,146, price is now £902 per person
£902
per person
27 Sept - 3 Oct
found 1 hour ago
Return flight included
London (LON) to Chicago (ORD)
8.6/10 Excellent! (1,007 reviews)
It's

Reviewed on 14 Jul 2026

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

4 out of 5
Downtown Chicago
Price was £1,333, price is now £1,081 per person
£1,081
per person
26 Sept - 2 Oct
found 4 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
8.8/10 Excellent! (2,504 reviews)
They first told us it was going to be $25 early check in fee and when we got there they said it was $75. I had to speak to an assistant manager. The bathroom in my room did not have a vent and it got extremely foggy and humid. Bathroom walls were in poor condition. The breakfast inside the hotel was great. The rooftop pool was okay but def not as pictured online. Location was great minus all the homeless people near by.

Reviewed on 14 Jul 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was £1,364, price is now £1,109 per person
£1,109
per person
2 Oct - 5 Oct
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,136 reviews)
Excellent location. Staff very nice. Room big and bed very comfortable. But noisy. As is all of Chicago. Trying to sell in room soap products for exorbitant prices tachy as hell. Rooftop lounge had sadly very short hours and limited open days. Seems a shame to waste such an opportunity.

Reviewed on 14 Jul 2026

Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago

4 out of 5
Downtown Chicago
Price was £1,195, price is now £972 per person
£972
per person
10 Sept - 14 Sept
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
8.8/10 Excellent! (2,343 reviews)
I didn't like that they did not have a microwave or fridge in the room. The microwave would have really been helpful. The beds and the room was to small

Reviewed on 13 Jul 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was £1,732, price is now £1,422 per person
£1,422
per person
20 Aug - 24 Aug
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)
We booked a two bedroom unit, but the unit clearly wasn't intended for a 2 bedroom. It was obviously a sitting area or something with a bed squeezed in. There was no vent so it made it impossible to shut the door, but then it was open to the living space and a full wall of windows. In addition, they list housekeeping as an amenity, and advertise one day or long term stays, however, for our 4 night stay, this didn't get housekeeping services. Meaning we had to get towels and coffee each day from the front desk, had piles of trash from cooking and such, and a heap of dirty towels from the week. Staff was friendly, but not really provided agency or capacity to do anything to fix the experience. Even a request for a fan to try to cool the space was impossible for them to solve (although they certainly had one for the front desk to keep staff comfortable).

Reviewed on 14 Jul 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
A busy city street with tall buildings, a bus, and cars.

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

Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is £144 per night from 3 Aug to 4 Aug
£144
3 Aug - 4 Aug
includes taxes & fees
8.8/10 Excellent! (2,847 reviews)
"This is the third time we’ve stayed, and every time we’ve enjoyed, property is well kept, nice rooms, great staff, wonderful breakfast, would definitely recommend!"

Reviewed on 14 Jul 2026

Hyatt Regency O'Hare Chicago
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is £146 per night from 27 Jul to 28 Jul
£146
27 Jul - 28 Jul
includes taxes & fees
8.2/10 Very good! (1,753 reviews)
"Nice property and location. Was charged 3 times for parking."

Reviewed on 14 Jul 2026

The Chicago Hotel Collection Ambassador Gold Coast
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is £234 per night from 26 Jul to 27 Jul
£234
26 Jul - 27 Jul
includes taxes & fees
9.2/10 Wonderful! (1,910 reviews)
"We came up to the hotel because my daughter was having surgery at a nearby hospital. Javier & Richard we're amazing at the valet in front of the hotel. Javier took care of all of our needs even brought the luggage up to our room upon check in. Stephen took Amazing care of our family during our stay. ..."

Reviewed on 14 Jul 2026

Omni Chicago Hotel
See all 4,536 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
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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 £902. 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.

Stay near popular Lower West Side attractions

Canalport Riverwalk Park

After visiting Canalport Riverwalk Park, make a plan to see the other sights and activities in Chicago. Experience the area's art scene and festivals.
See properties

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

£19
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£31
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.