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.
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3 out of 5
Downtown Chicago
Price was CA $1,729, price is now CA $1,215 per person
CA $1,215
per person
Aug 2 - Aug 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (1,008 reviews)
There's was no parking u have to pay but its first come first server and it was like like 65$ per night

Reviewed on May 10, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $2,256, price is now CA $1,425 per person
CA $1,425
per person
Aug 2 - Aug 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (472 reviews)
Beautiful clean place. Great safe location within proximity to restaurants and transportation around the city with fantastic views. Would recommend and stay here again.

Reviewed on May 14, 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was CA $2,893, price is now CA $1,935 per person
CA $1,935
per person
Aug 2 - Aug 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (984 reviews)
We loved the view from the 30th floor! The place was near the L, bus stops and walking distance to restaurants.. The bed was comfortable but it would be nice to have a table and lamp on both sides. The room seemed to be geared towards singles rather than couples. The espresso machine was a nice touch but fairly unusable for us. We ended up buying instant coffee and used the electric kettle. Sad that we couldn’t use the hot tub during our trip because it was closed for maintenance. But all in all, we were quite pleased with the apartment! Hubby spent a lot of time on the balcony enjoying the views. Highly recommend!

Reviewed on May 16, 2026

Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Downtown Chicago
Price was CA $2,411, price is now CA $1,667 per person
CA $1,667
per person
Aug 2 - Aug 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,225 reviews)
Nice hotel in a great location.

Reviewed on May 15, 2026

Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
Downtown Chicago
Price was CA $1,881, price is now CA $1,316 per person
CA $1,316
per person
Aug 2 - Aug 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (1,981 reviews)
Room temp was more easy to control manually (on/off).

Reviewed on May 17, 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 $184 per night from May 26 to May 27
CA $184
CA $218 total
May 26 - May 27
includes taxes & fees
8/10 Very Good! (10,145 reviews)
older and in a bit worn condition,, but in a great location the staff is fantastic.

Reviewed on May 17, 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $205 per night from May 25 to May 26
CA $205
CA $283 total
May 25 - May 26
includes taxes & fees
9.4/10 Exceptional! (4,174 reviews)
The breakfast menu was fresh, delicious, and there was such a good variety of items to choose from. The staff was pleasant & professional. Absolutely loved this hotel & will definitely vist again. There were tons of restaurants & shopping on the next block. Garretts popcorn right across the street ...

Reviewed on May 17, 2026

Hotel Riu Plaza Chicago
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundable
The price is CA $167 per night from May 25 to May 26
CA $167
CA $198 total
May 25 - May 26
includes taxes & fees
7.8/10 Good! (1,426 reviews)
After I tried checking in early, I came back later and the hotel gave away my room. I would not trust this hotel again.

Reviewed on May 17, 2026

The Chicago Hotel Collection - Magnificent Mile
See all 4,781 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 $1,215. 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
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

CA $60
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Flyover in Chicago

Flyover in Chicago

CA $31
per child
98% of travellers recommend
Flyover in Chicago
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.