Southwest Side Trip

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Top Southwest Side Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
per person
13 May - 18 May
found 19 hours ago
Return direct flight included
Kolkata (CCU) to Chicago (ORD)
8/10 Very Good! (1,433 reviews)
It was a relaxing stay in an area that is close to lots of good restaurants and close to the Magnificent Mile. We have stayed here many times and will continue to stay here as we come to visit Chicago.

Reviewed on 19 Feb 2025

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
per person
13 May - 18 May
found 19 hours ago
Return direct flight included
Kolkata (CCU) to Chicago (ORD)
8.8/10 Excellent! (1,915 reviews)
I’ll be back definitely

Reviewed on 18 Feb 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
13 May - 18 May
found 19 hours ago
Return direct flight included
Kolkata (CCU) to Chicago (ORD)
9/10 Wonderful! (287 reviews)
Amazing stay ! Love this property every time I’m in Chicago.

Reviewed on 20 Jan 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
13 May - 18 May
found 19 hours ago
Return direct flight included
Kolkata (CCU) to Chicago (ORD)
9.4/10 Exceptional! (1,514 reviews)
We loved everything about the hotel except that there was no place to get things like Tylenol or other convenience items requiring us to go out in the cold and try to walk somewhere

Reviewed on 18 Feb 2025

Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Downtown Chicago
per person
13 May - 18 May
found 19 hours ago
Return direct flight included
Kolkata (CCU) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
I was upset that the elevators were not working and it took a long to get to my room and the lobby. I would have appreciated communication about this ahead of time and would have switched hotels. Apparently it had been an issue for at least two weeks. The staff were amazing. The rooms were dark and small.

Reviewed on 14 Feb 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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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 ₹7,835 per night from 5 Mar to 6 Mar
₹7,835
₹9,198 total
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 ₹7,451 per night from 23 Feb to 24 Feb
₹7,451
₹8,746 total
includes taxes & fees
23 Feb - 24 Feb
7.8/10 Good! (8,511 reviews)
"A comfortable historical hotel, enjoyed the bar area, cocktails were good , would not recommend dining at the hotel. On Expedia it says it has parking and in and out privileges but this is not true, once you park you cant leave unless paying again (62$) . Had a paranormal experience in room 917 so ..."

Reviewed on 18 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 ₹11,218 per night from 23 Feb to 24 Feb
₹11,218
₹13,169 total
includes taxes & fees
23 Feb - 24 Feb
9.6/10 Exceptional! (1,661 reviews)
"Nice place but can be noisy."

Reviewed on 19 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 ₹151,248, 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.