Far Southeast Side Vacations from ￥355,338

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The Latest Far Southeast Side Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was ￥435,532, price is now ￥355,338 per person
￥355,338
per person
Oct 5 - Oct 9
found 7 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (523 reviews)

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4 out of 5
Downtown Chicago
Price was ￥680,311, price is now ￥538,766 per person
￥538,766
per person
Oct 9 - Oct 12
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (2,270 reviews)

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was ￥490,753, price is now ￥394,634 per person
￥394,634
per person
Oct 9 - Oct 12
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,566 reviews)

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was ￥467,276, price is now ￥379,566 per person
￥379,566
per person
Aug 25 - Aug 29
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 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 on Jul 14, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was ￥516,079, price is now ￥430,638 per person
￥430,638
per person
Aug 25 - Aug 29
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,910 reviews)
Trump is the best in town for families. Staff is awesome and pool is great. Very walkable. We go every summer

Reviewed on Jul 16, 2026

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
A man standing on a rocky outcrop with a large concrete structure in the background.

South Chicago

1 out of top 10 points of interest in this area

You'll enjoy the beaches and restaurants in South Chicago. You might want to make time for a stop at Lake Michigan or Mahalia Jackson Residence.

Find hotels in South Chicago

Find the Best Far Southeast Side Vacation Packages

Far Southeast Side Hotel Deals

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥31,482 per night from Jul 19 to Jul 20
￥31,482
￥37,429 total
Jul 19 - Jul 20
includes taxes & fees
8.2/10 Very Good! (1,763 reviews)
"We arrived into town at 9 am and they were able to get us into our room by 10:30am- amazing! We also loved the little rooftop terrace"

Reviewed on Jul 17, 2026

The Chicago Hotel Collection Ambassador Gold Coast
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥40,754 per night from Jul 26 to Jul 27
￥40,754
￥53,858 total
Jul 26 - Jul 27
includes taxes & fees
Omni Chicago Hotel
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥48,221 per night from Aug 16 to Aug 17
￥48,221
￥57,330 total
Aug 16 - Aug 17
includes taxes & fees
The Wade
See all 4,543 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.

Stay near popular Far Southeast Side attractions

Abbott Park

Abbott Park is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Amble around this vibrant area's lakeside or experience its acclaimed art scene.
See properties

What to do in Far Southeast Side

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

￥4,389
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

￥3,992
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Art Institute of Chicago

Art Institute of Chicago

￥6,502
per adult
92% of travellers recommend
Art Institute of Chicago
See all activities in Far Southeast Side

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 ￥355,338. 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.

Explore a world of travel with Expedia

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