Far Southeast Side Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Top Far Southeast Side Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
per person
Jun. 16 - Jun. 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,665 reviews)
Excellent location in the heart of the city. Room was clean and comfortable--seems like it was recently refurbished. Staff at the front desk were kind and approachable. Restaurant in house is also quite decent. Highly recommended.

Reviewed on Apr. 11, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun. 28 - Jul. 1
found 4 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,546 reviews)
Rooms were clean and spacious. Disappointed at the bar staff, not very engaging.

Reviewed on Apr. 6, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun. 13 - Jun. 15
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
9.6/10 Exceptional! (1,001 reviews)
Excellent staff! 5 stars all around the board!

Reviewed on Apr. 6, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
Jun. 16 - Jun. 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,605 reviews)
Absolutely loved this hotel and will definitely stay again! The rooms were so clean and cozy — the perfect place to unwind after I had been running around the city all day. The staff was also so friendly as well. I have to give Graciela a big shout out — I left my glasses in the lobby while I was checking out, she was so understanding and made it possible that I could get my glasses shipped to me within a few hours. Thank you!!

Reviewed on Apr. 12, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
Jun. 16 - Jun. 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (295 reviews)
Safe, beautiful suite that includes full kitchen, staff was very kind

Reviewed on Apr. 8, 2025

Where to stay in Far Southeast Side

Find the best Far Southeast Side areas and neighborhoods for the activities you enjoy most. Learn more about Far Southeast Side
Default Image

South Deering

1 out of top 10 points of interest in this area

Travelers enjoy South Deering for its churches and lake views. Consider checking out Harborside International Golf Center while you're in the area.

Find hotels in South Deering

Ready to book your vacation to Far Southeast Side?

 

Choose your dates

Far Southeast Side Hotel Deals

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 $188 per night from Apr. 20 to Apr. 21
CA $188
CA $220 total
includes taxes & fees
Apr 20 - Apr 21
8.2/10 Very Good! (3,872 reviews)
"Excellent quick friendly service! Staff is outstanding:)"

Reviewed on Apr. 11, 2025

Embassy Suites by Hilton Chicago Downtown River North
Swissotel - Chicago
Swissotel - Chicago
4.5 out of 5
323 E Wacker Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $216 per night from Apr. 13 to Apr. 14
CA $216
CA $295 total
includes taxes & fees
Apr 13 - Apr 14
8.8/10 Excellent! (2,038 reviews)
EXELLENT LOCATION
"Excellent location. We had a view of the lake and the river. Amazing stay. Resturant was five star and the bar downstairs cozy by fireplace. We parked in the garage upon arrival and walked every where. Will stay here again if ever back in Chicago."

Reviewed on Apr. 12, 2025

Swissotel - Chicago
Crowne Plaza Chicago West Loop by IHG
Crowne Plaza Chicago West Loop by IHG
3.5 out of 5
25 South Halsted Street, Chicago, IL
Fully refundable
The price is CA $128 per night from Apr. 20 to Apr. 21
CA $128
CA $150 total
includes taxes & fees
Apr 20 - Apr 21
8.6/10 Excellent! (1,009 reviews)
"Excellent property. Safe location. Convenient check in and check out."

Reviewed on Apr. 10, 2025

Crowne Plaza Chicago West Loop by IHG
See all 4,167 properties in Far Southeast Side
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 Far Southeast Side vacation package cost?
We make it easy to see the world, with Far Southeast Side vacation packages starting from as low as CA $645. You’ll have the flexibility to combine your preferred airlines, hotels and car rental. For the ultimate getaway, why not add a couple of tours and activities to your itinerary?
How do I get a cheap travel package to Far Southeast Side?
Combine your hotel and flight bookings, add extras such as a rental car or activities, and save with a Far Southeast Side vacation package. You won’t just enjoy impressive discounts on your getaway — you’ll have loads of choice at your fingertips too. When you book with Expedia, you can select from more than 550 partner airlines and 1,000,000 properties throughout the world. Your next grand adventure begins right here, right now!
What are the top hotels in Far Southeast Side?
When it comes to properties in Chatham Fields, Congress Plaza Hotel and LondonHouse Chicago, Curio Collection by Hilton are two terrific options. If you’re heading to Cheltenham, The Whitehall Hotel and Hyatt Regency Chicago will make you feel right at home.
How far in advance should I book my Far Southeast Side vacation?
It’s hard to pick the perfect time for airfares, but we normally say the earlier, the better. Most international flights on Expedia become available up to 12 months in advance. If you’re booking late, don’t worry. Cheap prices appear from time to time just weeks before departure dates.
What does an Expedia Far Southeast Side travel package include?
It comes down to what type of trip you have in the works. Far Southeast Side vacation deals can include car rentals, hotels and flights. You can mix and match to create the bundle that suits your needs. You can also add on experiences and activities after you’ve booked to pick up even bigger discounts.
What should I know before booking a Far Southeast Side travel package?
Bundling your bookings into a Far Southeast Side vacation package is the most convenient way to organize your trip. Not only that, you’ll save just for combining your hotels, flights and car rentals. Once you’ve booked, why not add on a tour or an activity?
Can I choose my airline with a Far Southeast Side Expedia vacation package?
Most definitely. Expedia has more than 550 airline partners to choose from worldwide. With such a big range of choice, finding the perfect carrier to whisk you off to Far Southeast Side won’t be hard.
If I'm not able to travel, can I cancel my Far Southeast Side vacation package?
You can. We get that even the best-laid plans can fail, so we’re happy to help if you have to make changes to your Far Southeast Side vacation package. It may be possible to cancel or amend your itinerary for free if you’ve booked within 24 hours. Your airline, hotel or car rental company may impose a fee if your booking was made more than 24 hours ago. Have a look at our Customer Service Portal for further information. Also, be sure to check your itinerary for the nitty-gritty on change fees.

Discover the most popular places to visit in Far Southeast Side

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
Magnificent Mile - River North which includes signage, a city and night scenes

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
Six Flags Great America featuring rides

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

What to do in Far Southeast Side

Flyover in Chicago

Flyover in Chicago

CA $55
per adult
98% of travellers recommend
Flyover in Chicago
River tour boat in Chicago

Architecture River Tour

CA $70
per adult
94% of travellers recommend
Architecture River Tour
Color Factory Chicago Ticket

Color Factory Chicago Ticket

CA $49
per adult
100% of travellers recommend
Color Factory Chicago Ticket
See all activities in Far Southeast Side
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.