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.
Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug. 9 - Aug. 12
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (1,126 reviews)
Only complaint was that housekeeping was a bit slow. A couple days our room was still not cleaned by 4:30, but someone did come eventually and we were on the 14th floor. Overall, staff was all helpful and polite, the space was clean and very convenient! I would stay here again.

Reviewed on Jun. 24, 2024

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep. 13 - Sep. 17
found 14 hours ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (1,006 reviews)
Carlos and whomever he was training at the front desk were fantastic! They were so pleasant to chat with and took the ordinary experience of checking-in and made it extraordinary. Thank you so much! The room was lovely/quiet, with a fantastic shower! The chocolate croissant at the coffee shop made us go back every morning.

Reviewed on Jun. 24, 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep. 13 - Sep. 17
found 14 hours ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (1,245 reviews)
Pleasant and centrally located for walking around to see the sights.

Reviewed on Jun. 25, 2024

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep. 13 - Sep. 17
found 14 hours ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
8.8/10 Excellent! (219 reviews)
Everything was great besides the hot tub being out of order during our stay.

Reviewed on Jun. 24, 2024

Chicago Marriott Downtown Magnificent Mile

Chicago Marriott Downtown Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep. 13 - Sep. 17
found 14 hours ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
8.4/10 Very Good! (1,000 reviews)
The hotel was excellent but the lobby bar was way over priced, $75 for 3 drinks so we didn’t go back to the bar however no other complaints!

Reviewed on Jun. 24, 2024

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

4 out of top 10 points of interest in this area

Known for its fascinating museums, stunning river views, and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Grant Park and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotel + flight trips 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 $186 per night from Jul. 1 to Jul. 2
CA $186
CA $218 total
includes taxes & fees
Jul 1 - Jul 2
7.6/10 Good! (7,110 reviews)
"Clean and good location."

Reviewed on Jun. 24, 2024

Congress Plaza Hotel
Embassy Suites by Hilton Chicago Downtown River North
Embassy Suites by Hilton Chicago Downtown River North
4 out of 5
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $248 per night from Jul. 1 to Jul. 2
CA $248
CA $292 total
includes taxes & fees
Jul 1 - Jul 2
8/10 Very Good! (2,437 reviews)
"Room was nice and spacious even with 4 of us in there! The bed was comfy, kids said the sleeper sofa was comfy everyone had a good time"

Reviewed on Jun. 23, 2024

Embassy Suites by Hilton Chicago Downtown River North
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $206 per night from Jun. 30 to Jul. 1
CA $206
CA $242 total
includes taxes & fees
Jun 30 - Jul 1
8.6/10 Excellent! (2,989 reviews)
"Amazing time great service next to everything convenient"

Reviewed on Jun. 24, 2024

River Hotel
See all 4,050 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.

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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 $898, 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

Image for Wrigley Field

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
Image for Six Flags Great America

Six Flags Great America

4.5/5(5 reviews)

Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.

Six Flags Great America
Image for Navy Pier

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

Image for Odyssey Lake Michigan Premier Dinner Cruise

Odyssey Lake Michigan Premier Dinner Cruise

CA $255
Per adult
76% of travellers recommend
Odyssey Lake Michigan Premier Dinner Cruise
Image for Chicago Pizza Tour

Chicago Pizza Tour

CA $121
Per adult
100% of travellers recommend
Chicago Pizza Tour
Image for Chicago: City Minibus Tour with Optional Architecture Cruise

Chicago: City Minibus Tour with Optional Architecture Cruise

CA $64
Per adult
98% of travellers recommend
Chicago: City Minibus Tour with Optional Architecture Cruise
See all activities in Chicago

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.