South Englewood Vacation Packages
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Top Holiday Package Deals in South Englewood
Price found within the past 48 hours. Click for updated prices.
Travelodge by Wyndham Downtown Chicago
Downtown Chicago
CA $684
per person
Oct 16 - Oct 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
7.6/10 Good! (2,711 reviews)
Parking was interesting and expensive, but hey, it’s Chicago. I appreciated the staff’s knowledge on other parking methods. Overall our 1 night stay was great! Room was neat and very clean.
Reviewed on Aug 13, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
CA $1,001
per person
Sep 21 - Sep 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
The service and rooms were excellent. Beds were comfortable and views were to die for. The food at Terra16 was a good but the wait times and food service took to long. Our fruit platter took over a half hour for breakfast. The spa was nice, but the lockers were hard to use or some worked and some did not lock. Front desk was exceptional and property was gorgeous. I would definitely stay again and was very happy with the staff who generally were attentive and kind.
Reviewed on Aug 13, 2026
Level Chicago Fulton Market
Downtown Chicago
CA $1,424
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
My go to place to stay. Luxurious, travel-friendly rooms, excellent pool/hot tub area outside, and great workout facilities. Fantastic location next to Fulton Market. The desk staff is always exceptional and helpful.
Reviewed on Aug 12, 2026
Where to stay in South Englewood
Find the best South Englewood areas and neighborhoods for the activities you enjoy most. Learn more about South Englewood
Downtown Chicago
4 out of top 10 points of interest in this area
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
The Loop
Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.
Magnificent Mile
Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.
River North
Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.
Lincoln Park
Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.
South Englewood Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
CA $151
CA $180 total
Sep 8 - Sep 9
includes taxes & fees
8/10 Very good! (10,295 reviews)
"Great location, hotel staff were friendly and helpful. Only complaint is the noise. I slept with earplugs in."
Reviewed on Aug 13, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
CA $199
CA $237 total
Aug 30 - Aug 31
includes taxes & fees
8/10 Very good! (1,979 reviews)
"When I arrived, the staff was unfriendly when I went upstairs to my room the elevator and the carpets in the hallway were pretty dirty. My room was a mess had to ask for clean sheets because mine had sweat marks on them there was leftover orange juice in the room the bathroom also was a mass had ..."
Reviewed on Aug 13, 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.
Frequently asked questions
How much does a South Englewood vacation package cost?
Our South Englewood packages, which start at just CA $684, are an ideal way to save big bucks. All you have to do is choose your preferred hotels, flights and more to create a customized itinerary.
How do I get a cheap travel package to South Englewood?
Bundle your flights and hotels with Expedia to save big on your next big adventure. With over 550 air carriers and 1,000,000 properties across the globe, your South Englewood vacation package can be customized exactly to suit your budget. With all those extra dollars, why not add one or two fun experiences and tours? It's an easy way to unlock even more savings. Your dream vacation in South Englewood is much closer than you thought!
Where should I stay in South Englewood?
A vacation in South Englewood wouldn't be complete without visiting Highland Community Bank, Carter G. Woodson Library and Final Call Newspaper Headquarters. Spend your nights near these top sights and make sightseeing a breeze.
How far in advance should I book my South Englewood vacation?
It all depends on the air carrier, but you can usually compare international fares on Expedia nearly a year in advance. While it's a good idea to book ahead of time, lucky travelers will sometimes score a cheaper flight just weeks before their intended journey.
What does an Expedia South Englewood travel package include?
That depends entirely on you. You can select from a variety of South Englewood packages, such as a rental car, hotel and flight. You can also book a hotel and a flight, or a rental car and a flight. Once you've made your booking, you can add the fun stuff like tours and activities. Whatever your ideal South Englewood getaway looks like, you're sure to save!
What should I know before booking a South Englewood travel package?
When you book your flights, hotels and car rentals together, you'll walk away with incredible discounts. Whether you're planning an island getaway in a villa or prefer to stay in a fancy hotel in the city, Expedia can make it happen for less.
Can I choose my airline with a South Englewood Expedia vacation package?
Yes, you sure can. We have more than 550 airline partners throughout the world, so select the carrier that suits your travel needs.
If I'm not able to travel, can I cancel my South Englewood vacation package?
Plans can change without warning, so yes. You may be able to cancel and rebook your South Englewood vacation package at no cost if you've booked in the last 24 hours. For older bookings, you can still cancel and rebook, but your car rental company, airline or hotel may charge additional fees. Want more information? Look up our Customer Service Portal. We're here to help make sure your getaway goes off without a hitch.
Things to do
Chicago: Navy Pier Centennial Wheel Ticket
CA $34
per adult
90% of travellers recommend
Wendella's Lake and River Architecture Tour
CA $63
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.