South Shore Vacations from ￥410,268

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The Latest South Shore Vacation Packages

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Jun 21 - Jun 27
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (1,152 reviews)
Every single person working at this facility was extremely polite and welcoming. I’ve stayed in so many hotels across the world and I have to say this was the best experience I’ve ever had staying at a hotel. Ordered food at 3am and it was fantastic. My cloths got folded in the short period of time my wife and I left the room and came back to a spotless room. Overall amazing experience. Will be staying here every time I come to Chicago.

Reviewed on Apr 16, 2024

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
per person
Jun 21 - Jun 27
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (3,485 reviews)
Very nice staff and great customer service! Would highly recommend the hotel bar, as the drinks and food were delicious! Only issue is that the deposit fee was not returned.

Reviewed on Apr 18, 2024

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
Jun 21 - Jun 27
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.8/10 Excellent! (206 reviews)
Thoroughly enjoyed my stay and my room. Will definitely book here again. Basic view of the courtyard but that was not important to me.

Reviewed on Mar 16, 2024

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
per person
Jun 21 - Jun 27
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.8/10 Exceptional! (1,007 reviews)
YOGA AND POOL AND ELEGANT LUNCH AREA PLUS LOVE MY SUITE !!!!

Reviewed on Apr 17, 2024

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
Jun 21 - Jun 27
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.6/10 Exceptional! (965 reviews)
Friendly and helpful staff, super comfy rooms and bed! Walked everywhere- easy walk to museum/aquarium, shopping, dining etc. will definitely be back!

Reviewed on Apr 15, 2024

Prices and availability subject to change. Additional terms may apply.

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

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Find hotels in Downtown Chicago

South Shore Hotel Deals

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 ￥17,444 per night from Apr 28 to Apr 29
￥17,444
per night
Apr 28 - Apr 29
7.6/10 Good! (6,547 reviews)
"I like it"

Reviewed on Apr 16, 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 ￥18,907 per night from Apr 22 to Apr 23
￥18,907
per night
Apr 22 - Apr 23
8.6/10 Excellent! (2,775 reviews)
Great hotel
"Hotel is in the best location. Right beside Michigan ave and the river walk is across the street. Excellent location. Short walk from most of the L trains and only a few extra blocks gets you to the Ohare blue line. Were given an early check in room which was nice and not expected. Staff were friendly. ..."

Reviewed on Apr 16, 2024

River 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 ￥23,142 per night from Apr 30 to May 1
￥23,142
per night
Apr 30 - May 1
8.2/10 Very Good! (1,848 reviews)
"Property was very nice"

Reviewed on Apr 18, 2024

Eurostars Magnificent Mile
See all 3,938 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 ￥410,268, 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.

Discover the most popular places to visit in South Shore

Image for Wrigley Field

Wrigley Field

4.5/5(2,128 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Image for McCormick Place

McCormick Place

4.5/5(1,805 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 Navy Pier

Navy Pier

4.5/5(4,870 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

Things to do

Image for Odyssey Lake Michigan Premier Dinner Cruise

Odyssey Lake Michigan Premier Dinner Cruise

￥23,662
Per adult
76% of travellers recommend
Odyssey Lake Michigan Premier Dinner Cruise
Image for Chicago Pizza Tour

Chicago Pizza Tour

￥11,048
Per adult
100% of travellers recommend
Chicago Pizza Tour
See all activities in Chicago

Other vacations you might like

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