Southwest Side Holidays from AU$3,630
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to AU$2,500 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Southwest Side Holiday Deals
Price found within the past 48 hours. Click for updated prices.
Our guide on 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 there might not be top attractions in Back of the Yards, you can explore the larger area and discover places 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.
Brighton Park
The restaurants and shopping are a few reasons travellers visit Brighton Park. Though there aren't many top sights in the neighbourhood, you can visit Plaza Garibaldi and United Center, a few notable attractions nearby.
Southwest Side Holiday
Southwest Side Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | O'Hare Intl. Airport (ORD) |
Our pick of the best Southwest Side Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
AU$179
22 Nov - 23 Nov
includes taxes & fees
8/10 Very good! (10,109 reviews)
"Great location and staff was helpful. Rooms were shabby and need some work."
Reviewed on 26 Oct 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
AU$205
22 Nov - 23 Nov
includes taxes & fees
8/10 Very good! (2,593 reviews)
"The property was a bit on the older side but overall it was really nice. The staff was good as well"
Reviewed on 26 Oct 2026
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
AU$196
22 Nov - 23 Nov
includes taxes & fees
8.8/10 Excellent! (5,569 reviews)
"Staff was exceptionally warm and missioned to serve the hotel's customers. Great place to stay."
Reviewed on 26 Oct 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 galleries.
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 studying the exhibits at Balzekas Museum of Lithuanian Culture in Chicago. Stroll along the lakeside in this vibrant area or visit 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 fascinating museums.
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
Skydeck Chicago at Willis Tower
AU$61
per adult
84% of travellers recommend
Frequently asked questions
How much does a Southwest Side holiday package cost?
From as little as AU$3,630, you can tailor make your Southwest Side holiday 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 holiday?
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 holiday!
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 holiday 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 holiday 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 holiday 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
- Hotels near Athenaeum Theatre
- Central Station Hotels
- Apartments in Chicago
- Accor Hotels in Chicago
- Cheap Hotels in Chicago
- Historic Hotels in Chicago
- Luxury Hotels in Chicago
- Chicago Hotels
- Motels in Chicago
- Hotels near Chicago Riverwalk
- Serviced Apartments in Chicago
- Hotels near Chicago Theatre
- Chinatown Hotels
- Cheap Hotels in Downtown Chicago
- Downtown Chicago Hotels
- Fairmont Hotels in Gold Coast
- Four Seasons Hotels in Gold Coast
- Swissotel Hotels in Gold Coast
- Hotels near Grant Park
- Magnificent Mile Hotels
- Hotels near McCormick Place
- Hotels near Michigan Avenue
- Hotels near Millennium Park
- Hotels near Navy Pier
- Near South Side Hotels
- River North Hotels
- Hotels near Soldier Field
- South Loop Hotels
- The Loop Hotels
- Theatre District Hotels
- United Center Hotels
- Hotels near University of Chicago
- Flights to Chicago
- Flights from Midway Intl.
- Flights from O'Hare Intl.
- Flights from Chicago
- Flights from Adelaide (ADL) to Chicago (ORD)
- Flights from Brisbane (BNE) to Chicago (ORD)
- Flights from Burbank (BUR) to Chicago (MDW)
- Flights from Charleston (CRW) to Chicago (MDW)
- Flights from Denver (DEN) to Chicago (MDW)
- Flights from New York (JFK) to Chicago (MDW)
- Flights from Los Angeles (LAX) to Chicago (ORD)
- Flights from New York (LGA) to Chicago (ORD)
- Flights from Melbourne (MEL) to Chicago (ORD)
- Flights from Perth (PER) to Chicago (ORD)
- Flights from San Francisco (SFO) to Chicago (ORD)
- Flights from Sydney (SYD) to Chicago (ORD)
- Abbott Park
- Apache Park
- Art Institute of Chicago
- Buckingham Fountain
- Visit Armour Square
- Visit Canaryville
- Visit Downtown Chicago
- Visit Gold Coast
- Visit Grand Boulevard
- Visit Jackson Park Highlands
- Visit Magnificent Mile
- Visit River North
- Chicago Riverwalk
- Visit South Loop
- Visit The Loop
- Visit West Loop
- Chicago Holidays
- Visit Chicago
- Cloud Gate
- Downtown Chicago Holidays
- Elk Grove Village Holidays
- Frank Lloyd Wright Historic District
- Garfield Park Conservatory
- Gold Coast Holidays
- Golf Holidays
- Grant Park
- Griffin Museum of Science and Industry
- Kathy Osterman Beach
- Legoland® Discovery Center
- Lincoln Hall
- Lincoln Park Zoo
- Lombard Holidays
- Millennium Park
- Montrose Beach
- Navy Pier
- Norma Holidays
- Oak Street Beach
- Pullman Holidays
- Six Flags Great America
- University of Illinois Chicago
- Waukegan BMX Track
- Willis Tower
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
