Far Southwest Side Vacations from ￥96,893

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The Latest Far Southwest Side Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4 out of 5
Downtown Chicago
Price was ￥127,701, price is now ￥96,893 per person
￥96,893
per person
Aug 19 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (2,270 reviews)
I stay again

Reviewed on Jul 14, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was ￥177,007, price is now ￥114,218 per person
￥114,218
per person
Aug 19 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (4,586 reviews)
Great vibe. Friendly and well trained staff. Loved the roof top bar. Generous breakfast included with room.

Reviewed on Jul 14, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was ￥175,272, price is now ￥121,629 per person
￥121,629
per person
Aug 19 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (2,566 reviews)
Very clean nice workers and amazing views

Reviewed on Jul 14, 2026

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Price was ￥432,973, price is now ￥334,033 per person
￥334,033
per person
Sep 23 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,819 reviews)
.

Reviewed on Jul 14, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was ￥399,552, price is now ￥309,262 per person
￥309,262
per person
Sep 23 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)
Room was clean area was fines. Staff was mediocre at best. Last night person seem disinterested and didn’t seem to want to speak. For the price we paid it was honestly not work it too me. Felt that they nickeled and dined you too death. No housekeeping for the entire 5 night. Crazy expensive for parking we had to make other arrangements which was a hassle since i was on crutches but we made it work. Even if we had parties on garage not elevator access. Will not be staying here again. Not worth the money, poor customer service. Had to get towels and empty trash daily. Very disappointing!!

Reviewed on Jul 13, 2026

Where to stay in Far Southwest Side

Find the best Far Southwest Side areas and neighborhoods for the activities you enjoy most. Learn more about Far Southwest Side
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Ashburn

The restaurants and churches are just a few features travelers like about Ashburn. If you want to do some sightseeing nearby, Childrens Museum of Oak Lawn and Wintrust Sports Complex are a few top places to visit.

Find hotels in Ashburn

Find the Best Far Southwest Side Vacation Packages

Far Southwest Side Hotel Deals

Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is ￥27,454 per night from Aug 3 to Aug 4
￥27,454
￥31,293 total
Aug 3 - Aug 4
includes taxes & fees
8.8/10 Excellent! (2,844 reviews)
"This is the third time we’ve stayed, and every time we’ve enjoyed, property is well kept, nice rooms, great staff, wonderful breakfast, would definitely recommend!"

Reviewed on Jul 14, 2026

Hyatt Regency O'Hare Chicago
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 ￥26,626 per night from Jul 27 to Jul 28
￥26,626
￥31,657 total
Jul 27 - Jul 28
includes taxes & fees
8.2/10 Very Good! (1,747 reviews)
"We decided to extend our stay and the staff were amazing. Very courteous !!!"

Reviewed on Jul 13, 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 ￥38,177 per night from Jul 26 to Jul 27
￥38,177
￥50,795 total
Jul 26 - Jul 27
includes taxes & fees
9.2/10 Wonderful! (1,907 reviews)
"."

Reviewed on Jul 14, 2026

Omni Chicago Hotel
See all 4,560 properties in Far Southwest 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 Southwest Side attractions

Highland Community Bank

Learn about the local history of Chicago when you take a trip to Highland Community Bank.
See properties

What to do in Far Southwest 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 Southwest Side

Frequently asked questions

How much does a Far Southwest Side vacation package cost?
Tailor make your Far Southwest Side vacation package from an affordable ￥96,893. Choose from any combination of rental cars, flights and hotels to craft the getaway you've been dreaming about. Remember to add on some activities and experiences!
How do I get a cheap travel package to Far Southwest Side?
Combining your flight and hotel with Expedia won't just save valuable time — it'll save you a nice amount too. A Far Southwest Side vacation package makes it a cinch to create your dream adventure. With more than 550 airlines all over the world to choose from, finding convenient flights that fit your schedule will be no sweat. On top of that, we have over 1,000,000 hotel options globally to pick from. Now that's what you call choice. Whatever your budget, Expedia can show you the world.
What are the top hotels in Far Southwest Side?
Check out the deals at Congress Plaza Hotel and LondonHouse Chicago, Curio Collection by Hilton in Chester Highlands. Any good Far Southwest Side itinerary has to include a stop in this great city!
How far in advance should I book my Far Southwest Side vacation?
It can be hard to know when is the perfect time to book your Far Southwest Side trip. But typically the earlier you book, the more affordable the prices. In some cases, you can reserve your flights and hotels nearly a year prior to departure. If you're considering a last-minute getaway, no need to panic! There are incredible bargains posted on Expedia every single day.
What does an Expedia Far Southwest Side travel package include?
Flights, hotels and car rentals — we connect you to the best deals. All you'll have to do is select your favorite combination. Once you've made your booking, you can add on the fun stuff like day tours and sightseeing activities. Our travel packages make it easy to customize an awesome Far Southwest Side trip.
What should I know before booking a Far Southwest Side travel package?
Whether it's relaxation or adventure you're chasing, a Far Southwest Side vacation package lets you organize your escape your way. Plus, you'll get access to great discounts just for combining your hotel with your rental car and flights. The more you bundle, the more you'll save!
Can I choose my airline with a Far Southwest Side Expedia vacation package?
With a vacation package, you're the one in charge. Whether you want to fly to Far Southwest Side in business or coach, simply pick from the available airline options. Expedia has access to more than 550 partner airlines globally.
If I'm not able to travel, can I cancel my Far Southwest Side vacation package?
If your vacation plans in Far Southwest Side have been upended, it's good to know that it is possible to cancel your booking. If you booked less than 24 hours ago, you may be eligible to receive a refund. If your booking is older than that, your airline, hotel or car rental company may charge a fee. For more details, check our Customer Service Portal.

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.