Southwest Side Vacations from ￥216,176

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The Latest Southwest Side Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Kinzie Hotel

Kinzie Hotel

4 out of 5
Downtown Chicago
Price was ￥262,220, price is now ￥216,176 per person
￥216,176
per person
Sep 21 - Sep 26
found 3 hours ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.2/10 Wonderful! (1,830 reviews)
Valet process was nice, but I don’t think the cost equates being charged 90 bucks. I was quoted 76 for valet. Confusinf

Reviewed on Aug 21, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ￥316,702, price is now ￥222,486 per person
￥222,486
per person
Sep 21 - Sep 26
found 3 hours ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.4/10 Exceptional! (2,316 reviews)
Great experience, highly recommended.

Reviewed on Aug 21, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was ￥334,044, price is now ￥238,532 per person
￥238,532
per person
Sep 21 - Sep 26
found 3 hours ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.4/10 Exceptional! (1,059 reviews)
Loved the atmosphere and friendly atmosphere

Reviewed on Aug 18, 2025

Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Downtown Chicago
Price was ￥334,132, price is now ￥238,994 per person
￥238,994
per person
Sep 21 - Sep 26
found 3 hours ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9/10 Wonderful! (1,005 reviews)
One of the tvs didnt work, and neither did the room phone. Dislike the texting communication, and having to go thru 3rd party just to call front desk.

Reviewed on Aug 17, 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was ￥332,652, price is now ￥239,308 per person
￥239,308
per person
Sep 21 - Sep 26
found 3 hours ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9/10 Wonderful! (654 reviews)
Hotel is located very centric. Nice view very quiet

Reviewed on Aug 22, 2025

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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Back of the Yards

2 out of top 10 points of interest in this area

While Back of the Yards might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Bridgeport Art Center and Zhou B Art Center.

Find hotels in Back of the Yards

Find the Best Southwest Side Vacation Packages

Southwest Side Hotel Deals

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 ￥27,724 per night from Sep 14 to Sep 15
￥27,724
￥32,547 total
Sep 14 - Sep 15
includes taxes & fees
7.8/10 Good! (8,963 reviews)
"Family had a great stay."

Reviewed on Aug 21, 2025

Congress Plaza Hotel
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥22,256 per night from Sep 3 to Sep 4
￥22,256
￥26,127 total
Sep 3 - Sep 4
includes taxes & fees
8.2/10 Very Good! (1,210 reviews)
"The room and view were super nice. Even with not being on the waterfront side of the build we werent disappointed. Check in staff could be nicer but the bar staff was excellent. Nice and informative for travelers. The pier was i. Walking distance. Food and shopping all around and spotless insude ..."

Reviewed on Aug 20, 2025

The Wade
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 ￥22,571 per night from Sep 4 to Sep 5
￥22,571
￥26,497 total
Sep 4 - Sep 5
includes taxes & fees
8.4/10 Very Good! (4,736 reviews)
"Great location for a quick getaway"

Reviewed on Aug 21, 2025

Embassy Suites by Hilton Chicago Downtown River North
See all 5,044 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.

Discover the most popular places to visit in Southwest Side

Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

4.5/5(2,128 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Magnificent Mile - River North showing night scenes, a city and signage

Michigan Avenue

4.5/5(332 reviews)

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Navy Pier featuring a sunset and rides

Navy Pier

4.5/5(4,870 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

What to do in Southwest Side

River tour boat in Chicago

Architecture River Tour

￥6,127
per adult
96% of travellers recommend
Architecture River Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

￥6,651
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

￥5,986
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Southwest Side

Frequently asked questions

How much does a Southwest Side vacation package cost?
From as little as ￥216,176, you can tailor make your Southwest Side vacation 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 vacation?
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 vacation!
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 vacation 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 vacation 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 vacation 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.