South Shore Holidays

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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 featuring 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

River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$186 per night from 29 Sep to 30 Sep
S$186
per night
29 Sep - 30 Sep
8.6/10 Excellent! (3,412 reviews)
"Booked last minute for a great rate and it was awesome for the price! Impeccable service from the front desk. Room was small but clean. You can't beat the area, downtown Chicago was fantastic! Only downside was $53 a day to valet park and the old guy parking cars was irate I didn't give him cash ..."

Reviewed on 22 Sep,2024

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 S$206 per night from 1 Oct to 2 Oct
S$206
per night
1 Oct - 2 Oct
7.6/10 Good! (7,875 reviews)
"Great location Good Service Some noises from maybe old machinery or renovation works. A/C needs more efficiency (New ones) But in overall and the prices its okay"

Reviewed on 23 Sep,2024

Congress Plaza Hotel
Eurostars Magnificent Mile
Eurostars Magnificent Mile
4 out of 5
660 North State Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$303 per night from 1 Oct to 2 Oct
S$303
per night
1 Oct - 2 Oct
8.6/10 Excellent! (2,572 reviews)
"Awesome staff!"

Reviewed on 24 Sep,2024

Eurostars Magnificent Mile
See all 3,618 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 holiday 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 holiday 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?
Holiday Makers 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 holiday?
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 travelling 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 holiday 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 holiday.
If I'm not able to travel, can I cancel my South Shore holiday package?
We understand — sometimes life doesn’t go according to plan. If you’ve booked a South Shore holiday 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

Image for 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
Image for Michigan Avenue

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
Image for Navy Pier

Navy Pier

4/5(125 reviews)

A waterfront entertainment strip with fun diversions for both young and old, with shops, restaurants and even a Ferris wheel.

Navy Pier

Things to do

Image for Flyover in Chicago

Flyover in Chicago

S$36
Per adult
96% of travellers recommend
Flyover in Chicago
Image for Architecture River Tour from Navy Pier

Architecture River Tour from Navy Pier

S$70
Per adult
94% of travellers recommend
Architecture River Tour from Navy Pier
Image for Chicago by Night: 90 Minute River and Lakefront Cruise

Chicago by Night: 90 Minute River and Lakefront Cruise

S$55
Per adult
86% of travellers recommend
Chicago by Night: 90 Minute River and Lakefront Cruise
See all activities in Chicago

More trip options

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