Southwest Side Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to NZ$2,400 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
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.
West Lawn
2 out of top 10 points of interest in this area
Travellers enjoy West Lawn for its restaurants and museums. Consider checking out Balzekas Museum of Lithuanian Culture while you're in the area.
Southwest Side Holiday
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
NZ$222
10 Nov - 11 Nov
includes taxes & fees
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
NZ$320
1 Nov - 2 Nov
includes taxes & fees
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Fully refundableReserve now, pay when you stay
NZ$271
1 Nov - 2 Nov
includes taxes & fees
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.
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
NZ$74
per adult
88% of travellers recommend
Frequently asked questions
How much does a Southwest Side holiday package cost?
From as little as , 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 SR Crown Hall
- Chicago Hotels
- Hotels near Auburn Park
- Englewood Hotels
- Hotels near Renaissance Society
- Clearing Hotels
- Little Village Hotels
- Hotels near Hyde Park Hair Salon
- Hotels near University of Chicago
- Hotels near Midway Intl.
- Near West Side Hotels
- Mckinley Park Hotels
- Evergreen Park Hotels
- West Englewood Hotels
- Washington Park Hotels
- Chinatown Hotels
- Bridgeport Hotels
- Hotels near McCormick Place
- Hotels near Arie Crown Theater
- Canaryville Hotels
- Cheap Hotels in South Side
- Business Hotels in South Side
- Cheap Hotels in Near South Side
- Lgbt Welcoming Hotels in Little Village
- Luxury Hotels in Hyde Park
- Cheap Hotels in Hyde Park
- Pet Friendly Hotels in Hyde Park
- Residences in South Side
- Apartments in Chicago 35th Street-Lou Jones-Bronzeville Station
- Holiday Homes in Southwest Side
- Cottages in Southwest Side
- La Quinta Inn & Suites Hotels in Southwest Side
- Kimpton Hotels in Southwest Side
- Sonesta Hotel in Southwest Side
- Hilton Hotels in Hyde Park
- Motel 6 Hotels in Hyde Park
- Motel 6 Hotels in Cicero
- Flights from Fort Wayne (FWA) to Chicago (MDW)
- Flights from Sacramento (SMF) to Chicago (MDW)
- Flights from St. Louis (STL) to Chicago (MDW)
- Flights from Anchorage (ANC) to Chicago (MDW)
- Flights from Vopnafjordur (VPN) to Chicago (MDW)
- Flights from Lake Of The Ozarks (AIZ) to Chicago (MDW)
- Flights from Kansas City (MCI) to Chicago (MDW)
- Flights from Omaha (OMA) to Chicago (MDW)
- Flights from Los Angeles (LAX) to Chicago (MDW)
- Flights from Atlanta (ATL) to Chicago (MDW)
- Flights from Midland (MAF) to Chicago (MDW)
- Flights from Boston (BOS) to Chicago (MDW)
- Flights from Huntsville (HSV) to Chicago (MDW)
- Flights from Harrisburg (MDT) to Chicago (MDW)
- Flights from Midway Intl.
- Garfield Park Conservatory
- Grant Park
- Pritzker Pavilion
- Art Institute of Chicago
- Bridgeport Art Center
- Downtown Chicago Holidays
- Willis Tower
- Copernicus Statue
- Mccormick Place
- Broadway Playhouse
- Hyde Park Hair Salon
- Robie House
- Field Museum of Natural History
- Seatgeek Stadium
- Adler Planetarium and Astronomy Museum
- Ernest Hemingway Museum and House
- Supreme Life Building
- Chicago Holidays
- Ohio Street Beach
- Crown Fountain
- Buckingham Fountain
- Harold Washington Library Center
- Millennium Park
- Richard J. Daley Center
- Zhou B Art Center
- Wintrust Arena
- Tribune Tower
- Obama's House
- Chicago Board of Trade Building
- Gold Coast Holidays
- Visit Gage Park
- Visit Fuller Park
- Visit Grace Abbott Homes
- Visit McKinley Park
- Visit Indian Village
- Visit Chicago Lawn
- Visit Bronzeville
- Visit Canaryville
- Visit Greater Grand Crossing
- Visit Hometown
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
