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 destinations in Far Southwest Side
Mount Greenwood
The Latest Far Southwest Side Vacation Packages
- Level Chicago Fulton Market
Sept 10 - Sept 14Level Chicago Fulton Market + Flight
Downtown Chicago4 nights4.0 star property9.2/10 - Wonderful (534 reviews)Roundtrip • Toronto (YTO) - Chicago (ORD)YTZ - MDW • Nonstop MDW - YTZ • NonstopCA $1,671CA $1,112found 1 day agoper traveller - Pendry Chicago
Sept 27 - Oct 3Pendry Chicago + Flight
Downtown Chicago6 nights4.5 star property9.2/10 - Wonderful (1,144 reviews)Roundtrip • Toronto (YTO) - Chicago (ORD)YTZ - MDW • Nonstop MDW - YTZ • NonstopCA $3,537CA $2,414found 0 hours agoper traveller - Level Chicago – Old Town
Sept 2 - Sept 6Level Chicago – Old Town + Flight
Downtown Chicago4 nights4.0 star property9.0/10 - Wonderful (504 reviews)"Good"Reviewed July 20, 2026Roundtrip • Toronto (YTO) - Chicago (ORD)YTZ - ORD • Nonstop ORD - YTZ • NonstopCA $2,049CA $1,426found 1 day agoper traveller - Thompson Chicago, by Hyatt
Sept 27 - Oct 3Thompson Chicago, by Hyatt + Flight
Downtown Chicago6 nights4.5 star property9.2/10 - Wonderful (1,380 reviews)"The hotel is nice and the rooms are generally good, but they are not keeping up with maintenance. The plastic backboard of the bed was worn and ripped (and gross looking), and the AC was very intense and uncomfortable. Carpet and walls in halls need repair. In short, the hotel is not worth the cost."Reviewed July 20, 2026Roundtrip • Toronto (YTO) - Chicago (ORD)YTZ - MDW • Nonstop MDW - YTZ • NonstopCA $2,719CA $1,945found 0 hours agoper traveller - JW Marriott Chicago
Sept 10 - Sept 14JW Marriott Chicago + Flight
Downtown Chicago4 nights4.5 star property9.2/10 - Wonderful (1,002 reviews)"After a 2hr flight delay due to the Canadian Wildfires we arrived in CHICAGO. Black Car Sedan Service pickup assured arrival to the hotel, I was completely amazed. The doorman assisted with exiting the limo to an absolutely clean street, curb and sidewalk. After a 50ft walk, we were at the front desk. Only two minutes later we were headed to the elevator doors that open before we can even reach to touch the call button. The door opens to the 4th floor and our room was less than 10 feet away..."Reviewed July 21, 2026Roundtrip • Toronto (YTO) - Chicago (ORD)YTZ - MDW • Nonstop MDW - YTZ • NonstopCA $1,599CA $1,147found 1 day agoper traveller
Discover the most popular places to visit in Far Southwest Side
Far Southwest Side Hotel Deals
Saratoga Motel By Capital O Near Midway Airport Chicago IL
Saratoga Motel By Capital O Near Midway Airport Chicago IL
Sable at Navy Pier Chicago, Curio Collection by Hilton
Sable at Navy Pier Chicago, Curio Collection by Hilton
Holiday Inn & Suites Chicago - Downtown by IHG
Holiday Inn & Suites Chicago - Downtown by IHG
Hilton Garden Inn Chicago Downtown South Loop
Hilton Garden Inn Chicago Downtown South Loop
The Chicago Hotel Collection Ambassador Gold Coast
The Chicago Hotel Collection Ambassador Gold Coast
Best Western Grant Park Hotel
Best Western Grant Park HotelFrequently Asked Questions
How much does a Far Southwest Side vacation package cost?
Tailor make your Far Southwest Side vacation package from an affordable CA $1,112. 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.