South Shore Holidays from £1,279

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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 Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was £1,934, price is now £1,279 per person
£1,279
per person
20 Jun - 25 Jun
just found
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Great location. Clean, comfortable, friendly staff.

Reviewed on 30 Mar 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,682, price is now £1,816 per person
£1,816
per person
30 May - 6 Jun
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Amazing experience will be back soon

Reviewed on 29 Mar 2026

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was £2,414, price is now £1,722 per person
£1,722
per person
30 May - 6 Jun
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (3,314 reviews)
Yes, the good looking young light haired gentleman at the front desk was especially helpful.

Reviewed on 30 Mar 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,860, price is now £2,099 per person
£2,099
per person
2 May - 9 May
found 10 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
Thank you for your exceptional hospitality

Reviewed on 29 Mar 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was £2,484, price is now £1,922 per person
£1,922
per person
2 May - 9 May
found 10 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,140 reviews)
Staff really friendly and hotel was clean and close to everything around the city can’t wait to come back.

Reviewed on 23 Mar 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

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

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 £102 per night from 5 Apr to 6 Apr
£102
5 Apr - 6 Apr
includes taxes & fees
8/10 Very Good! (10,021 reviews)
The hotel was not kept looking nice, very dinged up with peeling paint, bumpy carpet, and loose screws in locks. Looks like theyve tried to update and looks great in pictures. Staff wasnt rude but wasnt friendly either.

Reviewed on 30 Mar 2026

Congress Plaza Hotel
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 £121 per night from 5 Apr to 6 Apr
£121
5 Apr - 6 Apr
includes taxes & fees
9/10 Wonderful! (4,026 reviews)
yes

Reviewed on 30 Mar 2026

Hilton Chicago/Magnificent Mile Suites
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
Fully refundableReserve now, pay when you stay
The price is £130 per night from 13 Apr to 14 Apr
£130
13 Apr - 14 Apr
includes taxes & fees
8.6/10 Excellent! (5,805 reviews)
Breakfast was cold and hotel got a bit noisy. The staff was friendly and rooms was a little ou

Reviewed on 30 Mar 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,420 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 £1,279, 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

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(127 reviews)

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

Navy Pier
Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

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

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

£18
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£30
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
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.