Southwest Side Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to Rp16.000.000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    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
A waterfront promenade with a distinctive green-domed building, a city skyline in the background, and a clear blue sky.

Englewood

1 out of top 10 points of interest in this area

While you're strolling through Englewood, you may want to check out the beaches and restaurants. If you want to see more of the area, hop on the metro at Halsted Station or 63rd Station.

Find hotels in Englewood

Top hotels in Southwest Side

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 Rp2.099.668 per night from 24 Nov to 25 Nov
Rp2.099.668
Rp2.496.294 total
24 Nov - 25 Nov
includes taxes & fees
8/10 Very good! (10,151 reviews)
"The room was clean but tiny. Checkin was quick and they let us check in early. One thing I didn’t like is that we couldn’t control the thermostat. The location is awesome- close to everything!"

Reviewed on 10 Nov 2026

Congress Plaza Hotel
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 Rp2.097.317 per night from 7 Dec to 8 Dec
Rp2.097.317
Rp2.493.499 total
7 Dec - 8 Dec
includes taxes & fees
8/10 Very good! (2,695 reviews)
"Love this hotel! It was really nice, staff were very friendly and helpful! Restaurant and bar were perfect and open late. Paid breakfast buffet was nice as well!"

Reviewed on 10 Nov 2026

The Chicago Hotel Collection Ambassador Gold Coast
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is Rp1.917.434 per night from 10 Dec to 11 Dec
Rp1.917.434
Rp2.279.637 total
10 Dec - 11 Dec
includes taxes & fees
River Hotel
See all 4,886 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.

Stay near popular Southwest Side attractions

Marquette Park

9.4/10 (3 reviews)
After visiting Marquette Park, make a plan to see the other sights and activities in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed art galleries.
See properties

What to do in Southwest Side

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

Rp436.574
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

Rp718.640
per adult
92% of travellers recommend
Art Institute of Chicago
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

Rp760.636
per adult
92% of travellers recommend
Skydeck Chicago at Willis Tower
See all activities in Southwest Side

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.