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.
Four Seasons Hotel Chicago
Downtown Chicago
CA $6,031
per person
Oct 7 - Oct 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
Stayed for a weekend trip. Staff were extremely attentive and knowledgeable about the property and city in general. Room arrangement and amenities were excellent. Pool was larger than expected for a ‘high rise’ pool, and very family friendly - towels/locker room was well stocked. Location in relation to city is perfect for shopping and local excursions, but would recommend uber/lift to get around
Reviewed on Aug 16, 2026
Level Chicago Fulton Market
Downtown Chicago
CA $1,393
per person
Oct 27 - Oct 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
The property was wonderful and the proximity to Fulton Market can't be beat. The staff were always helpful when we had questions and when I faced an unexpected event they were understanding and accommodating. If you are looking for a space where you can spread out, be outdoors, and have beautiful surroundings, I highly recommend Level Fulton Market. We loved the pool and variety of outdoor spaces as well as lounge areas that allowed our group to have separate hang out areas. While you are of course in the heart of the city, the noise fell to the background and we had no issues sleeping or feeling rested. Everything was comfortable and clean. Easy walking to the best dining in the city.
Reviewed on Aug 17, 2026
Level Chicago – Old Town
Downtown Chicago
CA $1,152
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (512 reviews)
Beautiful property in great location! Would have definitely been a 5 but rooms facing the pool was very noisy
Reviewed on Aug 19, 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 $168
CA $199 total
Sep 7 - Sep 8
includes taxes & fees
8/10 Very good! (10,271 reviews)
"Room 406: Clean and quiet."
Reviewed on Aug 20, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
CA $197
CA $235 total
Aug 30 - Aug 31
includes taxes & fees
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
CA $347
CA $408 total
Sep 18 - Sep 19
includes taxes & fees
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 $790. 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.
Chicago Arts District
You can spend time exploring the galleries in Chicago Arts District in Chicago. Stroll along the lakeside or experience the fascinating museums in this vibrant area.
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.
Cooper Dual Language Academy
You can spend time browsing the exhibits at Cooper Dual Language Academy in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed art scene.
American Police Center & Museum
You can spend time exploring the galleries in American Police Center & Museum in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theater scene.
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.