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.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
Oct 3 - Oct 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (324 reviews)
I liked the hotel room's kitchen and it is very nice, however VERY small. The pool/amenities are also very nice. One major challenge was there was a last minute change to the location of our reservation from old town to fulton market. They did communicate the change and provided a discount, however, this occurred the day before our trip. The check-in process was also very disorganized and confusing. Information easily accessible in the reservation was not used, requiring extra check-in time. They told us a crib was available, and later found only a pack and play. I requested bedding for the pull out 4 times before someone brought them. Overall, management needs to improve their operations.

Reviewed on Jul. 21, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
Accessibility to Wendella Tours, shopping and the ‘L’ to go sightseeing

Reviewed on Jul. 24, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
Aug 29 - Sep 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
It's a beautiful and comfortable hotel.

Reviewed on Jul. 22, 2025

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
per person
Aug 29 - Sep 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,000 reviews)
The hotel was fine. But between the bed being the hardest bed ever and the music from the roof top club we didn't get much sleep.

Reviewed on Jul. 23, 2025

Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
Downtown Chicago
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (1,584 reviews)
FLIES!! Dining in the restaurant near the kitchen, getting carpet-bombed by a battalion of flies. Distracted while eating in restaurant with guest. Swarmed the next day while checking out. Staff oblivious. Said they “would” report, instead of they “HAD” reported.

Reviewed on Jul. 23, 2025

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 showing 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

Lower West Side Hotel Deals

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 CA $183 per night from Aug 18 to Aug 19
CA $183
CA $215 total
Aug 18 - Aug 19
includes taxes & fees
7.8/10 Good! (8,930 reviews)
"Unfortunately, the hotel doesn’t offer its own parking, so I had to pay over $60 per night at a nearby garage. Also, the bathroom wasn’t very clean — we found a lot of someone else’s hair when we checked in, which was disappointing. Other than that, the stay was good. The staff at the restaurant ..."

Reviewed on Jul. 22, 2025

Congress Plaza Hotel
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
505 N Michigan Ave, Chicago, IL
Fully refundable
The price is CA $332 per night from Aug 22 to Aug 23
CA $332
CA $433 total
Aug 22 - Aug 23
includes taxes & fees
9/10 Wonderful! (2,087 reviews)
"The staff was friendly and welcoming, the room was bigger than expected, my only issue was the bathroom shower must of had a leak around the edges because when I got out there was water all over the bathroom floor and I know I closed that glass door to shower. It happening to my husband when he showered ..."

Reviewed on Jul. 22, 2025

InterContinental Chicago Magnificent Mile by IHG
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $195 per night from Aug 24 to Aug 25
CA $195
CA $229 total
Aug 24 - Aug 25
includes taxes & fees
8.8/10 Excellent! (2,517 reviews)
"Close to Magnificent Mile"

Reviewed on Jul. 23, 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,656 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.
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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 $619. 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.

Things to do

Artisan Italian Pasta Class in Chicago

Artisan Italian Pasta Class in Chicago (Includes 3-Course Meal)

CA $163
per adult
Artisan Italian Pasta Class in Chicago (Includes 3-Course Meal)
Exclusive Sushi-Making Class in Chicago

Exclusive Sushi-Making Class in Chicago (Includes 3-Course Meal)

CA $163
per adult
Exclusive Sushi-Making Class in Chicago (Includes 3-Course Meal)
River tour boat in Chicago

Architecture River Tour

CA $67
per adult
96% of travellers recommend
Architecture River 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.