South Shore Holidays from £1,086
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Your South Shore Holiday
Booking a South Shore holiday package is a superb way to become acquainted with this neighbourhood. From its well-known places to its lesser-known gems, there's plenty to discover. When it's time to sightsee, you'll find lots of awesome attractions nearby including University of Chicago, Chicago Museum of Science and Industry and Robie House. Visit one or all during your trip to South Shore. Expedia will help you turn your dream South Shore holiday into reality, whatever your budget or travel plans.
Price found within the past 48 hours. Click for updated prices.
Kimpton Gray Hotel by IHG
Downtown Chicago
£1,086
per person
11 Nov - 15 Nov
found 14 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
Room was dated and showed signs of hard wear; front desk staff unfriendly; door men never once open the door for us from the street; area around hotel dirty.
Shay, the concierge was super nice though and the lobby was attractively decorated.
Reviewed on 4 Oct 2026
The Ritz-Carlton, Chicago
Downtown Chicago
£1,431
per person
28 Dec - 2 Jan
found 7 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,002 reviews)
The hotel was beautiful, the room was comfortable, and the staff was welcoming and attentive. Everything was clean and well maintained, and the location made it easy to get around the city. Overall, it was a really nice stay and I’d definitely consider coming back.
Reviewed on 24 Sept 2026
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
4 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.
Magnificent Mile
Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.
The Loop
Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.
River North
Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.
Lincoln Park
Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.
Top hotels in South Shore
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
£105
3 Nov - 4 Nov
includes taxes & fees
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
£150
1 Nov - 2 Nov
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
£128
1 Nov - 2 Nov
includes taxes & fees
8/10 Very good! (2,415 reviews)
"they over booked the hotel for my night that I was staying, so they did not have a room for me when I got to the hotel"
Reviewed on 4 Oct 2026
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 travel package cost?
The most affordable South Shore package is £1,086, so the trip of your dreams can become a reality — without it costing a fortune. Bundle flights, hotels and car rentals to build a package that matches your travel style.
If I'm not able to travel, can I cancel my South Shore travel package?
We totally understand that sometimes life doesn't go according to plan. If you've booked a South Shore travel package and have to cancel or change it, we can help. We recommend taking a look at our Customer Service Portal first for information. But in general, if you've booked your package within 24 hours, you may be able to cancel or change your itinerary at no cost. If it's more than 24 hours, your hotel, airline or car rental company may impose a charge.
How do I get a cheap travel package to South Shore?
Bundling your hotel and flight with Expedia won't just save precious time — it'll save you a nice amount too. A South Shore travel package makes it easy to put together the perfect trip. With more than 550 airlines all over the world to pick from, finding convenient flights that fit your schedule won't be an issue. In addition to that, we have over 1,000,000 hotels globally to take your pick of. Now that's what you call choice. Whatever your budget, Expedia will help show you the world.
Does Expedia offer Book Now, Pay Later South Shore holidays?
Your bank balance shouldn't get in the way of going on holiday, so Expedia has devised a solution to help. Now that we've teamed up with online lender Klarna, it's easier than ever to book your dream getaway without hurting your hip pocket. Klarna offers flexible payment options during the checkout process that take the worry out of budgeting for your trip. Check out these flexible payment options:
- Pay monthly holidays: If paying small amounts each month sounds best for you, Klarna can help. Paying in convenient monthly instalments will make that dream getaway possible.
- Pay in instalments holidays: With this Book Now, Pay Later option, Klarna makes it easy to pay off your trip across multiple transactions.
- Low deposit holidays: Pressing the "book now" button is much easier with this payment plan. Put down a small deposit on your holiday and then start working on your travel itinerary.
Where should I stay in South Shore?
Most people who travel to South Shore include both Millennium Park and Wrigley Field on their to-do lists. Why not book a hotel that's close to these fantastic attractions?
What are the top hotels in South Shore?
Get your holiday off to a good start by booking a room at Hyatt Regency Chicago. It's one of most sought-after properties in South Shore. Another option is The Godfrey Hotel Chicago.
How far in advance should I book my South Shore holiday?
While not all air carriers release ticket prices early, it's usually possible to look up international airfares on Expedia up to a year in advance. This is the time when you'll nab some fantastic bargains. If you've left everything to the last minute, there's a chance you could get lucky. Sometimes the cheapest prices emerge only weeks before departure.
What does an Expedia South Shore travel package include?
It comes down to what you're after. If you're travelling solo, you might decide to combine hotels and flights. Bringing the whole family to South Shore? A travel package including hotels, flights and rental cars might be a better fit. Expedia gives you the flexibility and freedom to tailor-make your travel package.
What should I know before booking a South Shore travel package?
Design deals to match your budget with an Expedia package. Hotels, airfares, rental cars — we're a one-stop shop for all of them. You'll save precious cash just by bundling your bookings. Whether you're embarking on a ski trip or sunning yourself on a warm beach, your ideal getaway is only a few clicks away.
Can I choose my airline with a South Shore Expedia travel package?
You can, and with over 550 airlines to pick from around the world, you have loads of choice. Scroll through the available options and find out which airline fits your budget and needs.
Stay near popular South Shore attractions
Rainbow Beach
Why not spend a lazy afternoon at Rainbow Beach during your trip to Chicago? Stroll along the beaches or visit the shops while you're in the area.
South Shore Cultural Center
Enjoy an outing to South Shore Cultural Center during your stay in Chicago. Amble around the area's beaches or visit its shops.
Stony Island Arts Bank
You can spend time exploring the galleries in Stony Island Arts Bank during your travels in Chicago. Stroll along the beaches or visit the shops while you're in the area.
Arthur Ashe Beach
Why not spend a lazy afternoon at Arthur Ashe Beach during your trip to Chicago? Stroll along the beaches or visit the shops while you're in the area.
ETA Creative Arts Foundation
You can enjoy a show at ETA Creative Arts Foundation during your stay in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed art galleries.
South Shore Golf Course
Enjoy a round of golf in Chicago at South Shore Golf Course. Amble around this vibrant area's lakeside or experience its acclaimed art galleries.
Things to do
Skydeck Chicago at Willis Tower
£32
per adult
88% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
£30
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.