South Shore Trips (flight + hotel)

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Where to stay in South Shore

Find the best South Shore areas and neighborhoods for the activities you enjoy most. Learn more about South Shore
Downtown Chicago showing a city

Downtown Chicago

5 out of top 10 points of interest in this area

Known for its fascinating museums, stunning river views, and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Michigan Avenue and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotel + flight trips in Downtown Chicago

Top hotels in South Shore

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 P7,592 per night from 25 Nov to 26 Nov
P7,592
P8,912 total
includes taxes & fees
Nov 25 - Nov 26
7.8/10 Good! (8,155 reviews)
Very clean
"Our stay was great! Easy check in, room and all areas were clean and smelled wonderful!"

Reviewed on Nov 23, 2024

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 P5,708 per night from 25 Dec to 26 Dec
P5,708
P6,700 total
includes taxes & fees
Dec 25 - Dec 26
8.6/10 Excellent! (3,547 reviews)
"I loved the view from my room! I loved that it is right in the middle of Downtown!!! I would stay here again."

Reviewed on Nov 21, 2024

River Hotel
Club Quarters Hotel, Central Loop, Chicago
Club Quarters Hotel, Central Loop, Chicago
4 out of 5
111 West Adams Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is P5,660 per night from 24 Dec to 25 Dec
P5,660
P6,645 total
includes taxes & fees
Dec 24 - Dec 25
8.4/10 Very Good! (3,264 reviews)
"This is a go-to hotel for me near a yearly event I participate in. It's the best value of any of the hotels in its immediate surrounding area."

Reviewed on Nov 21, 2024

Club Quarters Hotel, Central Loop, Chicago
See all 3,965 properties in South Shore
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 South Shore vacation package cost?
Starting from an incredible , you can handcraft your own South Shore package. Simply combine flights, hotels and car rentals and be rewarded with discounts.
How do I get a cheap travel package to South Shore?
Just think of all the awesome things you could do in South Shore with a pile of extra cash in your wallet. Watch your savings stack up when you combine your travel bookings into a South Shore vacation package. You have plenty of choice when it comes to booking with Expedia too. In fact, you can select from over 550 air carriers and 1,000,000 hotel options globally. Whether you’re enjoying a break with the entire family or going it alone, exploring South Shore is better with a package.
Where should I stay in South Shore?
Vacationers come from far and wide to experience University of Chicago and Chicago Museum of Science and Industry in South Shore. Stay within walking distance of these fantastic attractions and visit them whenever you please.
How far in advance should I book my South Shore vacation?
Search Expedia to compare international fares as soon as possible. You can usually purchase a seat up to 12 months before departure. If you can’t see your preferred air carrier, or you have to book last minute, don’t despair. Cheap tickets to South Shore sometimes emerge a few weeks before departure.
What does an Expedia South Shore travel package include?
That depends on what you want. If you’re traveling solo, you might decide to combine flights and hotels. Bringing the whole family to South Shore? A travel package including hotels, flights and rental cars might suit you better. Expedia gives you the freedom and flexibility to tailor-make your travel package.
What should I know before booking a South Shore travel package?
You’ll save plenty with an Expedia travel package. Bundle your airfares, rental cars and hotels and score fantastic discounts. Hotels aren’t your only option, however. We have island resorts, creek-side mountain cabins and even treehouses and ranches!
Can I choose my airline with a South Shore Expedia vacation package?
Expedia has access to more than 550 partner airlines worldwide, so you sure can! Simply select the carrier you want and put together your ideal South Shore vacation.
If I'm not able to travel, can I cancel my South Shore vacation package?
We understand — sometimes life doesn’t go according to plan. If you’ve booked a South Shore vacation package and have to amend or cancel it, we can help. It’s always worth checking out our Customer Service Portal first for information. But in general, if you’ve taken out your package within 24 hours, you may be able to cancel or change your itinerary at no cost. If it’s been longer than 24 hours, your airline, hotel or car rental company may impose a charge.

Popular places to visit

McCormick Place

McCormick Place

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
United Center

United Center

Catch an event at United Center during your trip to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theater scene.

United Center
Millennium Park showing modern architecture, autumn leaves and street scenes

Millennium Park

One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.

Millennium Park

Things to do

Flyover in Chicago

Flyover in Chicago

P2,217
Per adult
94% of travellers recommend
Flyover in Chicago
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

P2,594
Per adult
86% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
River tour boat in Chicago

Architecture River Tour

P3,130
Per adult
94% of travellers recommend
Architecture River Tour
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.