Southwest Side Holidays

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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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Clearing

Visitors to Clearing appreciate its restaurants. A visit to Wintrust Sports Complex and SeatGeek Stadium might round out your trip if you're looking to see more of the area.

Find hotels in Clearing

Top hotels in Southwest Side

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 €169 per night from 3 Aug to 4 Aug
€169
3 Aug - 4 Aug
includes taxes & fees
8.8/10 Excellent! (2,853 reviews)
"The hotel was exactly as advertised."

Reviewed on 15 Jul 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 €160 per night from 27 Jul to 28 Jul
€160
27 Jul - 28 Jul
includes taxes & fees
8.2/10 Very good! (1,751 reviews)
"Na"

Reviewed on 15 Jul 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 €315 per night from 26 Jul to 27 Jul
€315
26 Jul - 27 Jul
includes taxes & fees
Omni Chicago Hotel
See all 4,828 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.
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What to do in Southwest Side

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

€21
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

€40
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
Art Institute of Chicago

Art Institute of Chicago

€35
per adult
92% of travellers recommend
Art Institute of Chicago
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.

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