Southwest Side Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Top Southwest Side Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $1,221, price is now CA $812 per person
CA $812
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
Nice staff, easy check-in, and about an 8 minute walk to red line which can get you all over town. No complaints about our stay.

Reviewed on Jul 18, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,336, price is now CA $945 per person
CA $945
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,435 reviews)
Great experience the staff was super friendly and the hotel location was just amazing right in downtown Chicago. I will definitely be staying there again..

Reviewed on Jul 18, 2026

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 $3,157, price is now CA $2,244 per person
CA $2,244
per person
Oct 8 - Oct 12
found 6 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (2,566 reviews)
Very pleasant room

Reviewed on Jul 18, 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was CA $1,641, price is now CA $1,175 per person
CA $1,175
per person
Sep 6 - Sep 11
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.6/10 Exceptional! (135 reviews)

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $2,169, price is now CA $1,554 per person
CA $1,554
per person
Aug 24 - Aug 28
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (501 reviews)
Level hotels are awesome

Reviewed on Jul 18, 2026

Where to stay in Southwest Side

Find the best Southwest Side areas and neighborhoods for the activities you enjoy most. Learn more about Southwest Side
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Clearing

You'll appreciate the restaurants during your time in Clearing and you might want to plan a stop by Wintrust Sports Complex and SeatGeek Stadium while you're in the area.

Find hotels in Clearing

Ready to book your vacation to Southwest Side?

 

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Southwest Side Hotel Deals

Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is CA $265 per night from Aug 6 to Aug 7
CA $265
CA $302 total
Aug 6 - Aug 7
includes taxes & fees
Hyatt Regency O'Hare Chicago
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $266 per night from Aug 18 to Aug 19
CA $266
CA $317 total
Aug 18 - Aug 19
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $356 per night from Aug 9 to Aug 10
CA $356
CA $423 total
Aug 9 - Aug 10
includes taxes & fees
8.6/10 Excellent! (1,930 reviews)
"Why book here? LOCATION and competitive price. Why not? If you care about hospitality. This isn't going to be the place. Some of the front desk staff were impatient and border line dismissive. No decaf, despite a sign saying it was available. Just plan to go to Starbucks about a block away for coffee ..."

Reviewed on Jul 18, 2026

The Wade
See all 4,907 properties in Southwest 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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Stay near popular Southwest Side attractions

Marquette Park

9.4/10 (3 reviews)
After visiting Marquette Park, make a plan to see the other sights and activities in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed art scene.
See properties

What to do in Southwest Side

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $31
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

CA $35
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's Lake and River Architecture Tour

Wendella's Lake and River Architecture Tour

CA $64
per adult
94% of travellers recommend
Wendella's Lake and River Architecture Tour
See all activities in Southwest Side

Frequently asked questions

How much does a Southwest Side vacation package cost?
From as little as CA $812, you can tailor make your Southwest Side vacation package. Simply bundle hotels, flights and rental cars and we'll reward you with discounts.
How do I get a cheap travel package to Southwest Side?
You'll save loads of cash if you combine your car rentals, flights and hotels into a Southwest Side travel package. Sometimes cheap packages mean fewer options. But that's not the case with Expedia. We offer over 550 air carriers and 1,000,000 hotels across the globe, which means you'll always have plenty of options to choose from. Want to save even more? Add some exciting activities to your package deal to unlock even more bargains! After all, travel is about more than just getting to your destination.
What are the top hotels in Southwest Side?
Check out the deals at Congress Plaza Hotel and LondonHouse Chicago, Curio Collection by Hilton in Glendale. Any good Southwest Side itinerary should include this city!
How far in advance should I book my Southwest Side vacation?
You'll be rewarded with the widest variety at the cheapest prices by booking your adventure to Southwest Side early. Air carriers generally publish flights around a year in advance, so start your planning as soon as possible. Having said that, Expedia is constantly working to give you the best deals around, so it's never a bad time to book your dream vacation!
What does an Expedia Southwest Side travel package include?
With Expedia, you can select any combination of hotels, flights and car rentals to create your perfect Southwest Side package. Once you've made your booking, you can add on fun stuff like tours and activities. Remember, the more you bundle, the more dollars you'll save!
What should I know before booking a Southwest Side travel package?
Our prices are always low. However, you'll snap up an even better deal when you book your hotels, flights and car rentals together. With an Expedia package, you'll always get transparent pricing and lots of choice.
Can I choose my airline with a Southwest Side Expedia vacation package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines globally. Our packages give you the freedom to take your pick of available flight, hotel or activity options that suit you.
If I'm not able to travel, can I cancel my Southwest Side vacation package?
Yes you can, and we'll help you every step of the way. You may be able to amend or cancel your Southwest Side vacation package at no cost within 24 hours of booking. However, you may be charged a fee by your airline, hotel or car rental company for older bookings. If your travel plans suddenly change, visit our Customer Service Portal for more information.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.