Southwest Side Vacation Packages
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Top Southwest Side Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market
Downtown Chicago
CA $1,122
per person
Nov 25 - Nov 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (576 reviews)
El edificio es muy bueno, la atención del personal pésimo, siempre mal predispuestos para ayudar!
Reviewed on Oct 17, 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
Englewood
1 out of top 10 points of interest in this area
While you're strolling through Englewood, you may want to check out the beaches and restaurants. If you want to see more of the area, hop on the metro at Halsted Station or 63rd Station.
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.
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 $148
CA $176 total
Nov 11 - Nov 12
includes taxes & fees
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
CA $215
CA $256 total
Nov 1 - Nov 2
includes taxes & fees
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Fully refundableReserve now, pay when you stay
CA $182
CA $216 total
Nov 1 - Nov 2
includes taxes & fees
8/10 Very good! (2,418 reviews)
"terrible service"
Reviewed on Oct 18, 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.
Union Stock Yard Gate
You can find out about the history of Chicago with a trip to Union Stock Yard Gate.
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.
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.
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 fascinating museums.
What to do in Southwest Side
Skydeck Chicago at Willis Tower
CA $59
per adult
88% of travellers recommend
Wendella's Lake and River Architecture Tour
CA $63
per adult
94% of travellers recommend
Frequently asked questions
How much does a Southwest Side vacation package cost?
From as little as CA $1,063, 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.
Explore a world of travel with Expedia
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- Flights from Toronto (YYZ) to Chicago (MDW)
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- Art Institute of Chicago
- Wrigley Field
- Chicago Riverwalk
- Griffin Museum of Science and Industry
- Visit Chicago
- International Museum of Surgical Science
- Visit Downtown Chicago
- United Center
- Ernest Hemingway Museum and House
- Rosemont Vacations
- Navy Pier
- The Loop Vacations
- Chicago Theatre
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- Buckingham Fountain
- Lincoln Park Zoo
- Visit Magnificent Mile
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- Frank Lloyd Wright Historic District
- Visit The Loop
- Montrose Beach
- Ann and Robert H. Lurie Children's Hospital
- Willis Tower
- Lakeview Vacations
- 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.
