South Shore Holidays from £1,035

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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
Price was £1,319, price is now £1,035 per person
£1,035
per person
4 Sept - 8 Sept
found 1 day ago
Return flight included
Edinburgh (EDI) to Chicago (ORD)
8.2/10 Very good! (2,797 reviews)
I would definitely stay here again! Convenient location, walkable from most things. Staff were amazing and so helpful. Basic rooms, decent size. Very clean, great bar.

Reviewed on 1 Jul 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was £2,570, price is now £1,829 per person
£1,829
per person
23 Aug - 29 Aug
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (504 reviews)
The staff was extremely friendly and flexible regarding scheduling; this place is amazing.

Reviewed on 1 Jul 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was £1,629, price is now £1,268 per person
£1,268
per person
4 Sept - 8 Sept
found 1 day ago
Return flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (1,323 reviews)
Very unique motif

Reviewed on 1 Jul 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
Price was £1,652, price is now £1,309 per person
£1,309
per person
4 Sept - 8 Sept
found 1 day ago
Return flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (2,554 reviews)
Excellente

Reviewed on 1 Jul 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was £1,939, price is now £1,546 per person
£1,546
per person
4 Sept - 8 Sept
found 1 day ago
Return flight included
Edinburgh (EDI) to Chicago (ORD)
9.6/10 Exceptional! (1,899 reviews)
Great service

Reviewed on 30 Jun 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
A busy city street with tall buildings, a bus, and cars.

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 £109 per night from 6 Jul to 7 Jul
£109
6 Jul - 7 Jul
includes taxes & fees
8/10 Very good! (10,190 reviews)
"The rooms were bigger than expected! Very nice hotel and helpful staff. We arrived early than check in time was able to check in early for a fee. They had staff everywhere whom were very helpful with directions or if need any type of transportation. This was my second time staying here. Great location ..."

Reviewed on 2 Jul 2026

Congress Plaza Hotel
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is £162 per night from 5 Jul to 6 Jul
£162
5 Jul - 6 Jul
includes taxes & fees
9.2/10 Wonderful! (1,828 reviews)
"Very nice hotel. Great location, nice sized rooms."

Reviewed on 2 Jul 2026

Omni Chicago 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 £158 per night from 9 Jul to 10 Jul
£158
9 Jul - 10 Jul
includes taxes & fees
9/10 Wonderful! (4,478 reviews)
"R"

Reviewed on 2 Jul 2026

Hilton Chicago/Magnificent Mile Suites
See all 4,301 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 £1,035, 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.
See properties

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£18
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.