South Shore Holidays from £892

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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.
The Wade

The Wade

4.5 out of 5
Downtown Chicago
Price was £1,163, price is now £892 per person
£892
per person
27 Apr - 2 May
found 1 day ago
Return direct flight included
London (LGW) to Chicago (ORD)
8.4/10 Very Good! (1,444 reviews)
I had a great stay at the Wade Hotel in Chicago! The room was very clean and comfortable, and the staff was friendly, professional, and welcoming from check-in to check-out. The amenities were convenient, and the location made it easy to get around the city. I would definitely stay here again and recommend it to anyone visiting Chicago.

Reviewed on 9 Feb 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,398, price is now £926 per person
£926
per person
30 Mar - 6 Apr
found 23 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Friendly staff, tasteful room

Reviewed on 11 Feb 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was £1,310, price is now £937 per person
£937
per person
27 Apr - 2 May
found 1 day ago
Return direct flight included
London (LGW) to Chicago (ORD)
9.2/10 Wonderful! (347 reviews)
Hot tub wasn’t working(freezing cold) and no robes in my room. Need bigger roller carts and cheaper or free parking. Other than that the room, view, amenities were excellent.

Reviewed on 9 Feb 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was £1,293, price is now £979 per person
£979
per person
30 Mar - 6 Apr
found 23 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Muriel at the front desk was extremely helpful and courteous, wonderful historic art deco building right on Michigan Ave., great location and views, really nice, spacious and clean room. Chateau Carbide on the 24th floor is definitely worth checking out, nice cozy areas to hang out, sit on a couch and have a drink while enjoying great views of the city. We also got a free ride from the hotel to the Shedd Aquarium.

Reviewed on 31 Jan 2026

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Price was £1,394, price is now £1,068 per person
£1,068
per person
27 Apr - 2 May
found 1 day ago
Return direct flight included
London (LGW) to Chicago (ORD)
9.2/10 Wonderful! (1,404 reviews)
Great staff- very friendly

Reviewed on 9 Feb 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 featuring a city

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.

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 £152 per night from 14 Feb to 15 Feb
£152
14 Feb - 15 Feb
includes taxes & fees
8/10 Very Good! (9,876 reviews)
Staff was great, room service was quick and affordable. Room was spotless.

Reviewed on 10 Feb 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is £123 per night from 4 Mar to 5 Mar
£123
4 Mar - 5 Mar
includes taxes & fees
9.2/10 Wonderful! (3,313 reviews)
Love the room! Very ritzy!!

Reviewed on 8 Feb 2026

Hotel Riu Plaza Chicago
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 £88 per night from 23 Feb to 24 Feb
£88
23 Feb - 24 Feb
includes taxes & fees
8.4/10 Very Good! (5,643 reviews)
Positives- As my friend said as we went to breakfast “the people here are so nice and look happy to work here!” I agree! Eloisa (I hope that is correct-our bartender ) made happy hour on Friday night even happier! She was friendly and knowledgeable, suggesting drinks we hadn’t had before just by ...

Reviewed on 8 Feb 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,549 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 £892, 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

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

Wrigley Field
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

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
Navy Pier featuring a sunset and rides

Navy Pier

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

Navy Pier

Things to do

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
Flyover in Chicago

Flyover in Chicago

£28
per adult
98% of travellers recommend
Flyover in Chicago
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.