Southwest Side Holidays

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    Better together
    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

Where to stay in Southwest Side

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

2 out of top 10 points of interest in this area

Beaches and mountain views are just a few things travellers like about New City. A stop by Union Stock Yard Gate is also recommended if you've got time to explore the area.

Find hotels in New City

Top hotels in Southwest Side

River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$142 per night from 5 Mar to 6 Mar
S$142
includes taxes & fees
5 Mar - 6 Mar
8.6/10 Excellent! (3,795 reviews)
"I like the hotel at downtown area, it’s convenient for everything."

Reviewed on 18 Feb,2025

River Hotel
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 S$135 per night from 23 Feb to 24 Feb
S$135
includes taxes & fees
23 Feb - 24 Feb
7.8/10 Good! (8,516 reviews)
"All good"

Reviewed on 19 Feb,2025

Congress Plaza Hotel
L7 Chicago by LOTTE
L7 Chicago by LOTTE
4.5 out of 5
225 N Wabash Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$203 per night from 23 Feb to 24 Feb
S$203
includes taxes & fees
23 Feb - 24 Feb
9.6/10 Exceptional! (1,452 reviews)
"The hotel staff was nice and friendly!"

Reviewed on 17 Feb,2025

L7 Chicago by LOTTE
See all 4,625 properties in 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 Southwest Side holiday package cost?
From as little as , you can tailor make your Southwest Side holiday package. Simply bundle hotels, flights and rental cars and we’ll reward you with discounts.
How do I get a cheap travel package to Southwest Side?
You’ll save loads of cash if you combine your car rentals, flights and hotels into a Southwest Side travel package. Sometimes cheap packages mean fewer options. But that’s not the case with Expedia. We offer over 550 air carriers and 1,000,000 hotels across the globe, which means you’ll always have plenty of options to choose from. Want to save even more? Add some exciting activities to your package deal to unlock even more bargains! After all, travel is about more than just getting to your destination.
What are the top hotels in Southwest Side?
Check out the deals at Congress Plaza Hotel and LondonHouse Chicago, Curio Collection by Hilton in Glendale. Any good Southwest Side itinerary should include this city!
How far in advance should I book my Southwest Side holiday?
You’ll be rewarded with the widest variety at the cheapest prices by booking your adventure to Southwest Side early. Air carriers generally publish flights around a year in advance, so start your planning as soon as possible. Having said that, Expedia is constantly working to give you the best deals around, so it’s never a bad time to book your dream holiday!
What does an Expedia Southwest Side travel package include?
With Expedia, you can select any combination of hotels, flights and car rentals to create your perfect Southwest Side package. Once you’ve made your booking, you can add on fun stuff like tours and activities. Remember, the more you bundle, the more dollars you’ll save!
What should I know before booking a Southwest Side travel package?
Our prices are always low. However, you’ll snap up an even better deal when you book your hotels, flights and car rentals together. With an Expedia package, you’ll always get transparent pricing and lots of choice.
Can I choose my airline with a Southwest Side Expedia holiday package?
Yes — and it’s simple too. Expedia has access to more than 550 partner airlines globally. Our packages give you the freedom to take your pick of available flight, hotel or activity options that suit you.
If I'm not able to travel, can I cancel my Southwest Side holiday package?
Yes you can, and we’ll help you every step of the way. You may be able to amend or cancel your Southwest Side holiday package at no cost within 24 hours of booking. However, you may be charged a fee by your airline, hotel or car rental company for older bookings. If your travel plans suddenly change, visit our Customer Service Portal for more information.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.