Far Southwest Side Holidays from NZ$1,675

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The Latest Far Southwest Side Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
28 July - 2 Aug
found 1 day ago
Return flight included
Salt Lake City (SLC) to Chicago (ORD)
8.2/10 Very Good! (1,766 reviews)
Property was nice and clean today

Reviewed on 25 Jun. 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
28 July - 2 Aug
found 1 day ago
Return flight included
Salt Lake City (SLC) to Chicago (ORD)
9.4/10 Exceptional! (2,065 reviews)
Honestly one of the best places to stay at. Really loved this place.

Reviewed on 26 Jun. 2025

Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
28 July - 2 Aug
found 1 day ago
Return flight included
Salt Lake City (SLC) to Chicago (ORD)
9/10 Wonderful! (1,123 reviews)
Great location. Nice rooms

Reviewed on 22 Jun. 2025

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
28 July - 2 Aug
found 1 day ago
Return flight included
Salt Lake City (SLC) to Chicago (ORD)
9.4/10 Exceptional! (3,353 reviews)
Very comfortable hotel. Very responsive staff.

Reviewed on 25 Jun. 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
28 July - 2 Aug
found 1 day ago
Return flight included
Salt Lake City (SLC) to Chicago (ORD)
9.4/10 Exceptional! (1,613 reviews)
Pablo, the manager, got our great Chicago stay even better!

Reviewed on 24 Jun. 2025

Our guide on 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 a few reasons travellers visit Ashburn. Though there aren't many top sights in the neighbourhood, you can visit Chicago Ridge Shopping Mall and Balzekas Museum of Lithuanian Culture, a few notable attractions nearby.

Find hotels in Ashburn

Far Southwest Side Holiday

Our pick of the best Far Southwest 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 NZ$318 per night from 29 June to 30 June
NZ$318
29 June - 30 June
includes taxes & fees
8.4/10 Very Good! (4,263 reviews)
"Na"

Reviewed on 25 Jun. 2025

Embassy Suites by Hilton Chicago Downtown River North
InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHG
4.5 out of 5
505 N Michigan Ave, Chicago, IL
Fully refundable
The price is NZ$358 per night from 1 July to 2 July
NZ$358
1 July - 2 July
includes taxes & fees
9/10 Wonderful! (1,920 reviews)
"Our favorite Chicago hotel. The location is perfect for exploring the city, dining, and walking. My only complaint is that the condition of the pool was not nearly as clean and clear as usual."

Reviewed on 24 Jun. 2025

InterContinental Chicago Magnificent Mile by IHG
citizenM Chicago Downtown
citizenM Chicago Downtown
4 out of 5
80 East Wacker Place, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$238 per night from 29 June to 30 June
NZ$238
29 June - 30 June
includes taxes & fees
9.2/10 Wonderful! (3,230 reviews)
Citizen M Chicago
"We were very comfortable and the location was FANTASTIC! The only downside was not being able to get out of bed on both sides. Needed to climb over my husband. The room was small but had most of what we needed. There was a great " Iron Heaven" station on each floor that offered iron and steamer. ..."

Reviewed on 25 Jun. 2025

citizenM Chicago Downtown
See all 4,553 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.

Frequently asked questions

How much does a Far Southwest Side holiday package cost?
Tailor make your Far Southwest Side holiday package from an affordable NZ$1,675. 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 holiday 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 holiday?
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 favourite 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 holiday package lets you organise 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 holiday package?
With a holiday 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 holiday package?
If your holiday 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.

Discover the most popular places to visit in Far Southwest Side

Wrigley Field which includes a city, central business district and a sporting event

Wrigley Field

4.5/5(21 reviews)

A big piece of Chicago's soul, an ancient stadium that keeps alive the quirky, edgy madness of baseball.

Wrigley Field
Navy Pier

Navy Pier

4.5/5(64 reviews)

One of Chicago’s most popular attractions, especially on a hot day, with its fun fair, boats, circus and theatre.

Navy Pier
McCormick Place

McCormick Place

4.5/5(21 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place

What to do in Far Southwest Side

River tour boat in Chicago

Architecture River Tour

NZ$81
per adult
94% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

NZ$75
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

NZ$74
per adult
92% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Far Southwest Side
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.