South Chicago 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
The Latest South Chicago Vacation Packages
- Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination
Sept 11 - Sept 14Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination + Flight
Joliet3 nights3.5 star property8.6/10 - Excellent (1,013 reviews)"Nice setup, courteous staff, wasn’t expecting to have to pay $100 deposit on top of the money I paid Expedia, also an additional fee of $17 that Expedia did not cover even though they summed up all the charges before our stay. Seems to be a consistent issue with Expedia."Reviewed July 15, 2026Roundtrip • Toronto (YYZ) - Chicago (ORD)YYZ - ORD • Nonstop ORD - YYZ • NonstopCA $1,070CA $777found 1 day agoper traveller - Level Chicago – Old Town
Aug 24 - Aug 28Level Chicago – Old Town + Flight
Downtown Chicago4 nights4.0 star property9.0/10 - Wonderful (501 reviews)"Overall, I had a pleasant stay. The room was clean, and the staff were helpful. The property was comfortable and family-friendly. The only improvement would be better Wi-Fi and more breakfast options. I would still recommend this place."Reviewed July 14, 2026Roundtrip • Toronto (YTO) - Chicago (ORD)YTZ - MDW • Nonstop MDW - YTZ • NonstopCA $2,113CA $1,436found 1 day agoper traveller - Level Chicago Fulton Market
Sept 24 - Sept 27Level Chicago Fulton Market + Flight
Downtown Chicago3 nights4.0 star property9.2/10 - Wonderful (525 reviews)"Room was clean area was fines. Staff was mediocre at best. Last night person seem disinterested and didn’t seem to want to speak. For the price we paid it was honestly not work it too me. Felt that they nickeled and dined you too death. No housekeeping for the entire 5 night. Crazy expensive for parking we had to make other arrangements which was a hassle since i was on crutches but we made it work. Even if we had parties on garage not elevator access. Will not be staying here again. Not worth..."Reviewed July 13, 2026Roundtrip • Toronto (YTO) - Chicago (ORD)YTZ - MDW • Nonstop MDW - YTZ • NonstopCA $1,578CA $1,111found 7 hours agoper traveller - Hampton Inn & Suites Chicago Medical District UIC
Aug 24 - Aug 28Hampton Inn & Suites Chicago Medical District UIC + Flight
Near West Side4 nights2.5 star property9.6/10 - Exceptional (659 reviews)Roundtrip • Toronto (YTO) - Chicago (ORD)YTZ - MDW • Nonstop MDW - YTZ • NonstopCA $1,459CA $1,029found 1 day agoper traveller - Hotel Felix River North/Magnificent Mile
Oct 10 - Oct 14Hotel Felix River North/Magnificent Mile + Flight
Downtown Chicago4 nights4.0 star property8.2/10 - Very good (2,837 reviews)"It was very clean and in a nice location to our needs. The bed was comfortable the shower was AMAZING!!! Good water pressure and heat! Keep that up! Ice water and boxed water were available and we loved the fast elevators. Thank you friends. We will be back!"Reviewed July 16, 2026Roundtrip • Toronto (YTO) - Chicago (ORD)YTZ - MDW • Nonstop MDW - YTZ • NonstopCA $2,224CA $1,636found 23 hours agoper traveller
Frequently Asked Questions
How much does a South Chicago vacation package cost?
Live it up in South Chicago from just CA $777. Choose from a wonderful selection of hotels, flights and rental cars to suit your travel style. You can score even more discounts when you add a few sightseeing activities to your vacation package.
How do I get a cheap travel package to South Chicago?
Combine your flights and hotels, toss in extras such as activities or a rental car, and save with a South Chicago vacation package. You won't just pick up impressive discounts on your escape — you'll have lots of choice within your reach too. When you book through Expedia, you can select from more than 550 partner airlines and 1,000,000 hotels around the globe. Your dream vacation starts right here, right now!
Where should I stay in South Chicago?
With so much to do in South Chicago, it's a good idea to secure a room in a hotel close to its attractions. Calumet Beach, Calumet Park and Bronzeville Childrens Museum are some interesting ones to put on your must-see list.
How far in advance should I book my South Chicago vacation?
While not all airlines release ticket prices early, it's usually possible to compare international fares on Expedia up to 12 months in advance. This is the time you can bag some fantastic bargains. If you're purchasing tickets last minute, you might get lucky. Sometimes the cheapest prices emerge just weeks before departure.
What does an Expedia South Chicago travel package include?
From hotels and flights to car rentals, Expedia can help you craft a South Chicago package that fits you. Heading away for a week or longer? Consider a flight, rental car and hotel bundle. If you're taking a quick break, a hotel and flight deal could suit you better. Tours and activities can be added after you've booked. Our packages make it a cinch to plan and save.
What should I know before booking a South Chicago travel package?
You'll save big with an Expedia travel package. Bundle your airfares, rental cars and hotels and pick up fantastic discounts. You're not restricted to hotels, though. We've got island resorts, cozy city apartments and everything in between!
Can I choose my airline with a South Chicago Expedia vacation package?
Yes, of course. Expedia has access to more than 550 airline partners around the world, so fly with the carrier that best fits your budget and traveling style.
If I'm not able to travel, can I cancel my South Chicago vacation package?
If your vacation plans in South Chicago have changed, it's good to know that it's possible to cancel your booking. If you made your booking less than 24 hours ago, you may be eligible for a refund. If your booking was made more than 24 hours ago, your airline, hotel or car rental company may impose a cancellation fee. To find out more, check our Customer Service Portal.