Lower West Side Vacation Packages
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Top Holiday Package Deals in Lower West Side
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
CA $959
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (5,045 reviews)
Fantastic breakfast, great location, great room. The rooftop terrace was amazing, but we wishes we had known to make a reservation to be able to enjoy a drink there.
Reviewed on Aug 26, 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
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.
The Loop
Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.
Magnificent Mile
Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.
River North
Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.
Lincoln Park
Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.
Lower West Side Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
CA $145
CA $172 total
Sep 8 - Sep 9
includes taxes & fees
8/10 Very good! (10,324 reviews)
"The hotel is more ancient than I imagined. Things were so old and not maintained once you get to the hotel part. The lobby was the most maintained part of the hotel. The room was smaller than I would expect for the price. The bathroom was even smaller. I don’t believe what I paid was worth the price. ..."
Reviewed on Aug 27, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
CA $185
CA $220 total
Aug 31 - Sep 1
includes taxes & fees
8/10 Very good! (2,107 reviews)
"This hotel was so unappealing I didn’t feel comfortable sleeping there. It didn’t feel clean in the shower, I found an eyelash on my body that wasn’t mine. The furniture was stained, and there were unfinished renovation projects patched over throughout. The whole place needs a major overhaul. To ..."
Reviewed on Aug 27, 2026
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
CA $337
CA $395 total
Sep 18 - Sep 19
includes taxes & fees
8.4/10 Very good! (2,447 reviews)
"Very convenient, helpful staff"
Reviewed on Aug 26, 2026
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 Lower West Side vacation package cost?
Choose from any combination of hotels, flights and car rentals, and you can be vacationing in Lower West Side from just CA $791. And the more you bundle, the more cash you save. The vacation of your dreams has never been so affordable.
How do I get a cheap travel package to Lower West Side?
Combine your bookings with Expedia to save on your next exciting adventure. With over 550 partner airlines and 1,000,000 properties throughout the world, your Lower West Side vacation package can be customized exactly to suit your travel style. With all that extra money, why not throw in a few interesting tours and activities? It's an easy way to unlock even more discounts. Your dream vacation in Lower West Side is closer than you thought!
Where should I stay in Lower West Side?
Most people who travel to Lower West Side include both University of Illinois Chicago and United Center on their bucket lists. Why not reserve a hotel as close as possible to these iconic attractions?
How far in advance should I book my Lower West Side vacation?
Reserving your seat early with Expedia means one less thing to have to worry about. Most carriers advertise tickets up to a year in advance. This is often the cheapest time to book. If circumstances have left you booking late, low prices to Lower West Side sometimes become available a few weeks before departure.
What does an Expedia Lower West Side travel package include?
It comes down to what you're after. If you're traveling alone, you might decide to combine flights and hotels. Taking the whole family to Lower West Side? A travel package including flights, hotels and rental cars might be a better fit. Expedia gives you the freedom to build your own travel package.
What should I know before booking a Lower West Side travel package?
You can save a tidy sum by combining your hotels, airfares and rental cars. Once you've created your package, add on fun stuff like sightseeing tours or experiences. Your next awesome vacation is only a couple of clicks away.
Can I choose my airline with a Lower West Side Expedia vacation package?
Yes — that's the beauty of an Expedia vacation package. You're the boss! We have access to more than 550 partner airlines across the globe, so you have loads of choice when putting together your Lower West Side adventure.
If I'm not able to travel, can I cancel my Lower West Side vacation package?
We totally understand — life can throw you the odd curveball. If you've locked in a Lower West Side vacation package and have to cancel or amend it, we can help. It's always worth taking a look at our Customer Service Portal first for information. But in general, if you've booked your package in the last 24 hours, you may be able to amend or cancel your itinerary free of charge. If it's more than 24 hours, your hotel, airline or car rental company may impose a charge.
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.
Radius - Chicago
You can make plans for a show at Radius - Chicago during your trip to Chicago. Experience the area's art scene and festivals.
National Museum of Mexican Art
You can spend time exploring the galleries in National Museum of Mexican Art during your travels in Chicago. Experience the acclaimed art scene and entertainment choices in this vibrant area.
The Geraghty
After visiting The Geraghty, make a plan to see the other sights and activities in Chicago. Experience the area's art scene and festivals.
St Pius Church
After visiting St Pius Church, make a plan to see the other sights and activities in Chicago. Stroll along the lakeside or experience the fascinating museums in this vibrant area.
Mexican Fine Arts Center Museum
You can spend an afternoon studying the exhibits at Mexican Fine Arts Center Museum in Chicago. Stroll along the lakeside or experience the entertainment choices in this vibrant area.
Simone's
Simone's is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Experience the area's art scene and festivals.
Chicago Art Department
After visiting Chicago Art Department, make a plan to see the other sights and activities in Chicago. Experience the area's art scene and festivals.
Things to do
Chicago: Navy Pier Centennial Wheel Ticket
CA $34
per adult
90% of travellers recommend
Wendella's Lake and River Architecture Tour
CA $63
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.