South Shore Holidays from £1,022

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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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
per person
7 Sept - 13 Sept
found 18 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
8.2/10 Very Good! (1,785 reviews)
Decently clean, friendly staff and was in walking distance from almost everything I needed to get to. Will definitely be booking again

Reviewed on 27 Jun 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
12 Aug - 17 Aug
found 22 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (2,065 reviews)
Excellent staff that were helpful, friendly and fun with our young children

Reviewed on 28 Jun 2025

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
per person
6 Aug - 13 Aug
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (211 reviews)
other than the mold on the soap dispenser this hotel is beautiful

Reviewed on 27 Jun 2025

Nobu Hotel Chicago

Nobu Hotel Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
6 Aug - 13 Aug
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (678 reviews)
Great location. The service level was nowhere near a 5 star.

Reviewed on 26 Jun 2025

Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Downtown Chicago
per person
7 Sept - 13 Sept
found 18 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (1,034 reviews)
I would recommend this hotel. Overall a good experience. Beautiful property, location and restaurant. I stayed Sunday into Monday and found Starbucks located a few blocks away a good choice for coffee in the morning. Early morning coffee should be easy.

Reviewed on 23 Jun 2025

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

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

Top hotels in South Shore

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 £123 per night from 6 Jul to 7 Jul
£123
6 Jul - 7 Jul
includes taxes & fees
8.8/10 Excellent! (2,343 reviews)
"It was good, clean and large room"

Reviewed on 27 Jun 2025

Hilton Chicago/Magnificent Mile Suites
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 £161 per night from 2 Jul to 3 Jul
£161
2 Jul - 3 Jul
includes taxes & fees
9/10 Wonderful! (1,932 reviews)
"Elevators were really slow like uncomfortably slow and not efficient at all so"

Reviewed on 29 Jun 2025

InterContinental Chicago Magnificent Mile by IHG
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 £86 per night from 30 Jun to 1 Jul
£86
30 Jun - 1 Jul
includes taxes & fees
7.8/10 Good! (8,883 reviews)
"Great staff!"

Reviewed on 28 Jun 2025

Congress Plaza Hotel
See all 4,255 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.

All Inclusive Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

How much does a South Shore travel package cost?
The most affordable South Shore package is £1,022, 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.

Popular places to visit

Wrigley Field featuring a city, a sporting event and city views

Wrigley Field

4.5/5(40 reviews)

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

Wrigley Field
Navy Pier

Navy Pier

4/5(125 reviews)

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

Navy Pier
Magnificent Mile - River North which includes street scenes, signage and night scenes

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

Things to do

River tour boat in Chicago

Architecture River Tour

£36
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

£33
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

£33
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. Flight-inclusive packages are ATOL protected.