Far Southwest Side Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 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
Top Far Southwest Side Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
CA $1,022
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (5,106 reviews)
The Riu Plaza is more of a 2-3 star hotel staying there this week. Here are the reasons I experienced. Bed linen and towels dirty for 2 days having to be changed by cleaning staff. One bathroom sink stopped up. We visited the restaurant on the roof which had a nice ambiance but the service was extremely slow with the spicy wings I ate that did not agree with my stomach. Unfortunately there is no business center on the premises. The self-parking garage the hotel recommended is very scary.
Overall, we were highly disappointed with the 3 night stay at the Riu Plaza and do not recommend it.
Reviewed on Sep 6, 2026
Grand Geneva Resort & Spa
CA $1,063
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (1,009 reviews)
Our villa was clean and we had zero issues with it - everything worked. Laundry was easy to use, and we were even able to get room service. Somewhat unexpected given that the villas are detached from the main lodge. The only thing to know is that villas guests *do not* have access to the main outdoor pool, which means one cannot use the outdoor food/bar there. There is a small pool for each set of villas, but it is small, and minimally equipped. Again, no issues with it - perfectly nice, you just need to bring your own food.
Reviewed on Sep 4, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
CA $988
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (2,685 reviews)
Arrived to a confusion about the room and pricing through Expedia. Staff was helpful and took care of it! Got the pricing we were promised and had a great stay! Me and my fiance had a great time!
Reviewed on Sep 5, 2026
Where to stay in Far Southwest Side
Find the best Far Southwest Side areas and neighborhoods for the activities you enjoy most. Learn more about Far Southwest Side
Ashburn
The restaurants and churches are just a few features travelers like about Ashburn. If you want to do some sightseeing nearby, Wintrust Sports Complex and Chicago Ridge Shopping Mall are a few top places to visit.
Beverly
The restaurants and churches are just a few features travelers like about Beverly. If you want to do some sightseeing nearby, Beverly Arts Center and Harborside International Golf Center are a few top places to visit.
Auburn Gresham
2 out of top 10 points of interest in this area
While visiting Auburn Gresham, you might make a stop by sights like Highland Community Bank and Final Call Newspaper Headquarters.
Washington Heights
1 out of top 10 points of interest in this area
The restaurants and shopping are just a few things visitors like about Washington Heights. Carter G. Woodson Library and Dr. Percy Julian Residence are worthwhile spots to check out, and you can hop on the metro at 95th Street - Longwood Station or 103rd Street Washington Heights Station to get around the larger area.
Morgan Park
1 out of top 10 points of interest in this area
Travelers enjoy Morgan Park for its restaurants and shopping. Consider checking out Beverly Arts Center while you're in the area.
Ready to book your vacation to Far Southwest Side?
Far Southwest Side Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
CA $141
CA $168 total
Sep 8 - Sep 9
includes taxes & fees
8/10 Very good! (10,284 reviews)
"The hotel is in a great location. All major bus and train routes are within two blocks. Rooms are good, area is safe and I would stay again."
Reviewed on Sep 6, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
CA $210
CA $250 total
Sep 30 - Oct 1
includes taxes & fees
Kasa Magnificent Mile Chicago
One Superior Place Chicago IL
9.4/10 Exceptional! (888 reviews)
"We thoroughly enjoyed our stay at Kasa- check in instructions were clear and hassle free. The unit was spacious and clean, with a terrific view. Highly recommended!"
Reviewed on Sep 4, 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 Far Southwest Side attractions
Beverly Arts Center
Beverly Arts Center is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Make some time to visit the shops while you're in the area.
Final Call Newspaper Headquarters
Find out about the history of Chicago with a stop at Final Call Newspaper Headquarters.
Highland Community Bank
Learn about the local history of Chicago when you take a trip to Highland Community Bank.
Carter G. Woodson Library
You can enjoy some culture when you stop by Carter G. Woodson Library in Chicago. Make some time to visit the shops while you're in the area.
What to do in Far 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 Far Southwest Side vacation package cost?
Tailor make your Far Southwest Side vacation package from an affordable CA $720. Choose from any combination of rental cars, flights and hotels to craft the getaway you've been dreaming about. Remember to add on some activities and experiences!
How do I get a cheap travel package to Far Southwest Side?
Combining your flight and hotel with Expedia won't just save valuable time — it'll save you a nice amount too. A Far Southwest Side vacation package makes it a cinch to create your dream adventure. With more than 550 airlines all over the world to choose from, finding convenient flights that fit your schedule will be no sweat. On top of that, we have over 1,000,000 hotel options globally to pick from. Now that's what you call choice. Whatever your budget, Expedia can show you the world.
What are the top hotels in Far Southwest Side?
Check out the deals at Congress Plaza Hotel and LondonHouse Chicago, Curio Collection by Hilton in Chester Highlands. Any good Far Southwest Side itinerary has to include a stop in this great city!
How far in advance should I book my Far Southwest Side vacation?
It can be hard to know when is the perfect time to book your Far Southwest Side trip. But typically the earlier you book, the more affordable the prices. In some cases, you can reserve your flights and hotels nearly a year prior to departure. If you're considering a last-minute getaway, no need to panic! There are incredible bargains posted on Expedia every single day.
What does an Expedia Far Southwest Side travel package include?
Flights, hotels and car rentals — we connect you to the best deals. All you'll have to do is select your favorite combination. Once you've made your booking, you can add on the fun stuff like day tours and sightseeing activities. Our travel packages make it easy to customize an awesome Far Southwest Side trip.
What should I know before booking a Far Southwest Side travel package?
Whether it's relaxation or adventure you're chasing, a Far Southwest Side vacation package lets you organize your escape your way. Plus, you'll get access to great discounts just for combining your hotel with your rental car and flights. The more you bundle, the more you'll save!
Can I choose my airline with a Far Southwest Side Expedia vacation package?
With a vacation package, you're the one in charge. Whether you want to fly to Far Southwest Side in business or coach, simply pick from the available airline options. Expedia has access to more than 550 partner airlines globally.
If I'm not able to travel, can I cancel my Far Southwest Side vacation package?
If your vacation plans in Far Southwest Side have been upended, it's good to know that it is possible to cancel your booking. If you booked less than 24 hours ago, you may be eligible to receive a refund. If your booking is older than that, your airline, hotel or car rental company may charge a fee. For more details, check our Customer Service Portal.
Explore a world of travel with Expedia
- Magnificent Mile Hotels
- Hotels near Auburn Park
- Downtown Chicago Hotels
- Hotels near Wrigley Field
- Hotels near United Center
- The Loop Hotels
- Cheap Hotels in Chicago
- Hotels near O'Hare Intl.
- Auburn Gresham Hotels
- Hotels near Midway Intl.
- 3 Star Hotels in Chatham
- Hotels near Navy Pier
- Pet-Friendly Hotels in Chicago
- Fulton Market Hotels
- Hotels near McCormick Place
- Motels in Chicago
- West Loop Hotels
- All Inclusive Resorts and in Chicago
- Hotels near Grant Park
- Hotels with a Pool in Chicago
- Lincoln Park Hotels
- Hotels near Art Institute of Chicago
- Beverly Hotels
- Hotels near Soldier Field
- Hotels with Free Airport Shuttle in Chicago
- Hotels near Millennium Park
- Hotels with Free Parking in Chicago
- River North Hotels
- Hotels with Free Breakfast in Chicago
- Chicago Hotels
- Cheap Hotels in Downtown Chicago
- Marriott Hotels & Resorts in Chicago
- Flights from Regina (YQR) to Chicago (ORD)
- Flights from Calgary (YYC) to Chicago (ORD)
- Flights from Winnipeg (YWG) to Chicago (ORD)
- Flights from Toronto (YYZ) to Chicago (ORD)
- Flights from Philadelphia (PHL) to Chicago (MDW)
- Flights from Seattle (SEA) to Chicago (ORD)
- Flights from O'Hare Intl.
- Flights from Detroit (DTW) to Chicago (ORD)
- Flights from Edmonton (YEG) to Chicago (ORD)
- Flights from Montreal (YUL) to Chicago (MDW)
- Flights from Ottawa (YOW) to Chicago (ORD)
- Flights from Chicago
- Flights from Kitchener (YKF) to Chicago (ORD)
- Flights from Saskatoon (YXE) to Chicago (ORD)
- Flights from Montreal (YUL) to Chicago (ORD)
- Flights from Ottawa (YOW) to Chicago (MDW)
- Flights from Detroit (DTW) to Chicago (MDW)
- Flights to Chicago
- Flights from Toronto (YTZ) to Chicago (MDW)
- Flights from Midway Intl.
- Flights from Buffalo (BUF) to Chicago (ORD)
- Flights from London (YXU) to Chicago (ORD)
- Flights from Calgary (YYC) to Chicago (MDW)
- Flights from Windsor (YQG) to Chicago (ORD)
- Flights from Toronto (YYZ) to Chicago (MDW)
- Flights from Vancouver (YVR) to Chicago (ORD)
- Flights from Hamilton (YHM) to Chicago (ORD)
- Flights from New York (LGA) to Chicago (ORD)
- Flights from Halifax (YHZ) to Chicago (ORD)
- Chicago Theatre
- Willis Tower
- Lincoln Park Zoo
- Griffin Museum of Science and Industry
- Buckingham Fountain
- Grant Park
- The Loop Vacations
- Visit Cook County
- 875 North Michigan Avenue
- Chicago Riverwalk
- Visit Chicago
- Phoenix Vacations
- United Center
- Centennial Beach
- Ernest Hemingway Museum and House
- Marina City
- Golf Vacations
- Visit Downtown Chicago
- Frank Lloyd Wright Historic District
- Art Institute of Chicago
- Navy Pier
- Montrose Beach
- Unity Temple
- Wrigley Field
- Visit The Loop
- International Museum of Surgical Science
- Downtown Chicago Vacations
- Water Tower Place
- Chicago Vacations
- Robie House
- Millennium Park
- Lakeview Vacations
- Ann and Robert H. Lurie Children's Hospital
- Garfield Park Conservatory
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
