South Shore Trips (flight + hotel)

Photo by Jihad F. Saleh
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    Better together
    Save up to P 3,118 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy
    Plan, book, and manage your trip all in one place

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 hotels in Downtown Chicago

Top hotels in South Shore

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
The price is P8,798 per night from Jul 1 to Jul 2
P8,798
P10,327 total
Jul 1 - Jul 2
includes taxes & fees
8.4/10 Very Good! (4,268 reviews)
"Great location, we enjoyed our stay"

Reviewed on Jun 23, 2025

Embassy Suites by Hilton Chicago Downtown River North
InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHG
4.5 out of 5
505 N Michigan Ave, Chicago, IL
Fully refundable
The price is P9,031 per night from Jul 1 to Jul 2
P9,031
P12,444 total
Jul 1 - Jul 2
includes taxes & fees
9/10 Wonderful! (1,912 reviews)
"Requested two queen beds twice through customer service. Did not honor request. Room was nice besides we put the thermostat as low as possible and was still not cool at night. Great location and overall good stay"

Reviewed on Jun 22, 2025

InterContinental Chicago Magnificent Mile by IHG
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 out of 5
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is P7,786 per night from Jul 6 to Jul 7
P7,786
P9,140 total
Jul 6 - Jul 7
includes taxes & fees
8.8/10 Excellent! (2,335 reviews)
"The staff were amazing! Very friendly and helpful."

Reviewed on Jun 23, 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,232 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
Six Flags Great America which includes rides

Six Flags Great America

Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.

Six Flags Great America
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

River tour boat in Chicago

Architecture River Tour

P2,740
per adult
94% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

P2,507
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

P2,507
per adult
92% of travellers recommend
Chicago By Night River & Lake Cruise
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.