Lower West Side Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*

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Top Holiday Package Deals in Lower West Side

Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was CA $1,691, price is now CA $1,132 per person
CA $1,132
per person
Jun 20 - Jun 23
found 13 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Very quiet, really clean and staff was great

Reviewed on Apr 2, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was CA $2,003, price is now CA $1,269 per person
CA $1,269
per person
Jun 5 - Jun 8
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
I travelled for my birthday and I had an awesome time. The staff were very friendly and kind. All staff were extremely helpful and attentive. They remembered my birthday and each greeting felt special and personal. I looked forward to breakfast each morning to enjoy their tasty spread. My room was very comfortable and clean with amazing views . The hotel is located in a great area where you walk to great places with the bus stop around the corner. I was looking forward to the roof top restaurant however it was closed. That’s my only disappointment but I would definitely visit again God spare life

Reviewed on Apr 2, 2026

Hotel Chicago Downtown, Autograph Collection by Marriott

Hotel Chicago Downtown, Autograph Collection by Marriott

4 out of 5
Downtown Chicago
Price was CA $1,944, price is now CA $1,327 per person
CA $1,327
per person
May 5 - May 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
Nice hotel with friendly staff! Housekeeping very helpful and kind. It does seem the front desk was understaffed for the size of hotel and how busy it was. Was hard to get call answered when phoned desk.

Reviewed on Mar 30, 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was CA $2,018, price is now CA $1,405 per person
CA $1,405
per person
May 5 - May 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (2,076 reviews)
Everything was perfect

Reviewed on Mar 26, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $1,738, price is now CA $1,244 per person
CA $1,244
per person
Jun 9 - Jun 12
found 14 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (421 reviews)
Garage area very dark and unsafe

Reviewed on Mar 31, 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

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 $150 per night from Apr 16 to Apr 17
CA $150
CA $177 total
Apr 16 - Apr 17
includes taxes & fees
8/10 Very Good! (10,039 reviews)
Slightly old

Reviewed on Apr 1, 2026

Congress Plaza Hotel
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 $190 per night from Apr 12 to Apr 13
CA $190
CA $223 total
Apr 12 - Apr 13
includes taxes & fees
9/10 Wonderful! (4,033 reviews)
Overall a great place. My only issue was that they charged us for 3 nights of valet @82.00, but we only had a car there for one night.

Reviewed on Apr 1, 2026

Hilton Chicago/Magnificent Mile Suites
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 CA $198 per night from Apr 12 to Apr 13
CA $198
CA $232 total
Apr 12 - Apr 13
includes taxes & fees
8.6/10 Excellent! (5,803 reviews)
Positives: The staff was friendly, professional, and very helpful throughout my stay. Negatives: Unfortunately, my experience had a few issues. I didn’t receive the suite I had booked for the first night and had to switch rooms the next day, which was quite inconvenient. The bathroom also had a persistent ...

Reviewed on Apr 1, 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,758 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 $1,132. 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

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $37
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $55
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Color Factory Chicago Ticket

Color Factory Chicago Ticket

CA $47
per adult
94% of travellers recommend
Color Factory Chicago Ticket
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.