South Englewood Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*

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Top Holiday Package Deals in South Englewood

Price found within the past 48 hours. Click for updated prices.
La Banque Hotel

La Banque Hotel

4 out of 5
Price was CA $1,208, price is now CA $772 per person
CA $772
per person
Apr 24 - Apr 28
found 18 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
9.4/10 Exceptional! (447 reviews)
Courteous Staff, clean, one of the most beautiful and interesting hotel. The history is amazing. The restaurant is delicious and the community is outstanding. Plan to return in the spring.

Reviewed on Jan 26, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was CA $1,895, price is now CA $1,101 per person
CA $1,101
per person
May 17 - May 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
This was a great stay! Really enjoyed the breakfast! Only down side was the shower. Water did not get hot and water pressure was horrible. Otherwise would have been 5 stars!

Reviewed on Feb 21, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $1,919, price is now CA $1,141 per person
CA $1,141
per person
May 13 - May 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (347 reviews)
Room smelled like food but overall very clean, very great service and staff both night and morning shift.

Reviewed on Feb 16, 2026

JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,455, price is now CA $980 per person
CA $980
per person
Apr 24 - Apr 28
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
9.2/10 Wonderful! (1,000 reviews)
The room was great and clean , there was a toilet issue but the staff members gladly were readily available to fix it all ! The amenities including the hot tub, and pool as well as the in room service breakfast was 5/5 . Would absolutely stay here again .

Reviewed on Feb 17, 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was CA $1,535, price is now CA $1,054 per person
CA $1,054
per person
May 13 - May 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (766 reviews)
Clean room and spacious.

Reviewed on Feb 18, 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 showing a city

Downtown Chicago

5 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.

Find hotels in Downtown Chicago

South Englewood Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $122 per night from Feb 27 to Feb 28
CA $122
CA $143 total
Feb 27 - Feb 28
includes taxes & fees
8/10 Very Good! (9,912 reviews)
Everything was clean and neat.

Reviewed on Feb 19, 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $136 per night from Mar 4 to Mar 5
CA $136
CA $198 total
Mar 4 - Mar 5
includes taxes & fees
9.2/10 Wonderful! (3,355 reviews)
The room was excellent

Reviewed on Feb 16, 2026

Hotel Riu Plaza Chicago
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $190 per night from Feb 27 to Feb 28
CA $190
CA $263 total
Feb 27 - Feb 28
includes taxes & fees
8.4/10 Very Good! (2,642 reviews)
Great room, friendly staff.

Reviewed on Feb 19, 2026

Hilton Chicago
See all 4,675 properties in South Englewood
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a South Englewood vacation package cost?
Our South Englewood packages, which start at just CA $772, 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.

Discover the most popular places to visit in South Englewood

Wrigley Field featuring central business district, a city and a sporting event

Wrigley Field

4.5/5(158 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

Michigan Avenue

4.5/5(19 reviews)

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Navy Pier featuring a sunset and rides

Navy Pier

4.5/5(459 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

Things to do

Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $55
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Flyover in Chicago

Flyover in Chicago

CA $52
per adult
98% of travellers recommend
Flyover in Chicago
Color Factory Chicago Ticket

Color Factory Chicago Ticket

CA $46
per adult
96% of travellers recommend
Color Factory Chicago Ticket
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.