Southwest Side Trip

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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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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 hotel + flight trips in New City

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 ₹7,962 per night from 9 Jan to 10 Jan
₹7,962
₹9,346 total
includes taxes & fees
9 Jan - 10 Jan
7.8/10 Good! (8,376 reviews)
"Beautiful area, although not many great food options around. The hotel is pretty outdated, but charming. Also, constant sirens in and around the area…. don’t know how the locals handle it! Although, the transportation is amazingly connected but kinda sketch."

Reviewed on 6 Jan 2025

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ₹8,229 per night from 20 Jan to 21 Jan
₹8,229
₹9,660 total
includes taxes & fees
20 Jan - 21 Jan
8.6/10 Excellent! (3,681 reviews)
"Loved it"

Reviewed on 8 Jan 2025

River Hotel
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 ₹8,379 per night from 26 Jan to 27 Jan
₹8,379
₹9,836 total
includes taxes & fees
26 Jan - 27 Jan
8.2/10 Very Good! (3,452 reviews)
Weekend Getaway
"Checkin was quick and smooth Room was clean and nice. Plenty of amenities and restaurants and bars in the area."

Reviewed on 5 Jan 2025

Embassy Suites by Hilton Chicago Downtown River North
See all 4,012 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.

Popular places to visit

Magnificent Mile - River North which includes street scenes, signage and night scenes

Michigan Avenue

4.5/5(14 reviews)

You can find the perfect gifts to bring home 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
Wrigley Field featuring a city, a sporting event and city views

Wrigley Field

4.5/5(40 reviews)

Chicago’s world-renowned baseball ground, Wrigley Field is an iconic stadium where you can learn about the all-American sport and even catch a game.

Wrigley Field
McCormick Place

McCormick Place

4.5/5(36 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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.