Southwest Side Vacation Packages
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Top Southwest Side Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Emily Hotel
Downtown Chicago
CA $1,633
per person
Oct 19 - Oct 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,339 reviews)
Love staying at the Emily! Everyone is always so friendly and helpful and the loft style rooms are super comfortable and spacious. The neighborhood has the best food and coffee of every type within walking distance and many clubs as well including Garcia's and Broken Hearts.
Reviewed on Aug 31, 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
Garfield Ridge
Be sure to check out the restaurants and churches while you're strolling through Garfield Ridge, and hop on the metro at Midway Station to see more of the surrounding area.
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.
Back of the Yards
2 out of top 10 points of interest in this area
While Back of the Yards might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Bridgeport Art Center and Zhou B Art Center.
McKinley Park
1 out of top 10 points of interest in this area
Be sure to check out the monuments and shopping while you're strolling through McKinley Park, and hop on the metro at 35th-Archer Station to see more of the surrounding area.
West Lawn
2 out of top 10 points of interest in this area
Travelers enjoy West Lawn for its restaurants and museums. Consider checking out Balzekas Museum of Lithuanian Culture while you're in the area.
Ready to book your vacation to Southwest Side?
Southwest Side Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
CA $142
CA $169 total
Sep 8 - Sep 9
includes taxes & fees
8/10 Very good! (10,250 reviews)
"The lady who checked me in was extremely helpful and really nice."
Reviewed on Sep 2, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
CA $158
CA $188 total
Sep 7 - Sep 8
includes taxes & fees
Kasa Magnificent Mile Chicago
One Superior Place Chicago IL
9.4/10 Exceptional! (886 reviews)
"I felt comfortable during my stay at Kasa. There was a lot of room space and having a balcony was great"
Reviewed on Sep 2, 2026
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.
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.
Balzekas Museum of Lithuanian Culture
10.0/10 (1 review)
You can spend time exploring the galleries in Balzekas Museum of Lithuanian Culture in Chicago. Stroll along the lakeside in this vibrant area, or check out its top-notch restaurants.
S.S. Peter and Paul Church
After visiting S.S. Peter and Paul Church, make a plan to see the other sights and activities in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theater scene.
Union Stock Yard Gate
You can find out about the history of Chicago with a trip to Union Stock Yard Gate.
Ephraim Bajar Cultural Center
Enjoy an outing to Ephraim Bajar Cultural Center during your stay in Chicago. Amble around the area's parks or visit its churches.
What to do in Southwest Side
Wendella's Lake and River Architecture Tour
CA $62
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
CA $56
per adult
94% of travellers recommend
Frequently asked questions
How much does a Southwest Side vacation package cost?
From as little as CA $1,080, 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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- Art Institute of Chicago
- Wrigley Field
- Chicago Riverwalk
- Griffin Museum of Science and Industry
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- International Museum of Surgical Science
- Visit Downtown Chicago
- United Center
- Ernest Hemingway Museum and House
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- Navy Pier
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- Chicago Theatre
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- Buckingham Fountain
- Lincoln Park Zoo
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- Frank Lloyd Wright Historic District
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- Montrose Beach
- Ann and Robert H. Lurie Children's Hospital
- Willis Tower
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- 875 North Michigan Avenue
- Grant Park
- Robie House
- Marina City
- Water Tower Place
- Downtown Chicago Vacations
- Unity Temple
- Millennium Park
- Chicago Vacations
- Garfield Park Conservatory
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
