A cityscape with a mix of modern and older buildings, a large body of water in the background, and a clear sky.

South Shore Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to €900 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest South Shore Holiday Packages

Price found within the past 48 hours. Click for updated prices.
  • 29 Dec - 3 Jan

    Hotel Felix River North/Magnificent Mile + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    8.4/10 - Very good (3,187 reviews)
    "Charged for an extra night that we didn’t stay and called and was told a reimbursement was completed. Five days later, the full charge for the night we didn’t stay posted in my account and with no reimbursement. When I called again, was told there was nothing they could do because the reimbursement was “released” and I would have to wait to talk to a manager when they arrived which would not be until the nighttime hours."
    Reviewed November 14, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • Direct ORD - DUB • Direct
    €1,271
    €1,046
    per traveller
    found 6 hours ago
    Hotel Felix River North/Magnificent Mile
  • 29 Dec - 3 Jan

    Hotel Saint Clair- Magnificent Mile + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    8.6/10 - Excellent (2,413 reviews)
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • Direct ORD - DUB • Direct
    €1,472
    €1,113
    per traveller
    found 6 hours ago
    Hotel Saint Clair- Magnificent Mile
  • 29 Dec - 3 Jan

    Swissotel - Chicago + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    9.0/10 - Wonderful (3,585 reviews)
    "LOVE this hotel! Location is perfect and you can walk everywhere! Just wished they had a pool"
    Reviewed November 14, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • Direct ORD - DUB • Direct
    €1,507
    €1,213
    per traveller
    found 6 hours ago
    Swissotel - Chicago
  • 29 Dec - 3 Jan

    Sports Illustrated Resorts Chicago + Flight

    Downtown Chicago
    5 nights
    3.5 star property
    9.0/10 - Wonderful (1,541 reviews)
    "Very clean and comfortable. Valet was helpful and kind"
    Reviewed November 13, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • Direct ORD - DUB • Direct
    €1,367
    €1,116
    per traveller
    found 6 hours ago
    Sports Illustrated Resorts Chicago
  • 29 Dec - 3 Jan

    InterContinental Chicago Magnificent Mile by IHG + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    9.2/10 - Wonderful (3,428 reviews)
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • Direct ORD - DUB • Direct
    €1,399
    €1,159
    per traveller
    found 6 hours ago
    InterContinental Chicago Magnificent Mile by IHG

Where to stay in South Shore

Find the best South Shore areas for the activities you enjoy most.

Downtown Chicago

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.

Discover the most popular places to visit in South Shore

South Shore Hotel Deals

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 holiday package cost?

Starting from an incredible €1,046, you can handcraft your own South Shore package. Simply combine flights, hotels and car rentals and be rewarded with discounts.

How do I get a cheap travel package to South Shore?

Just think of all the awesome things you could do in South Shore with a pile of extra cash in your wallet. Watch your savings stack up when you combine your travel bookings into a South Shore holiday package. You have plenty of choice when it comes to booking with Expedia too. In fact, you can select from over 550 air carriers and 1,000,000 hotel options globally. Whether you're enjoying a break with the entire family or going it alone, exploring South Shore is better with a package.

Where should I stay in South Shore?

Holiday Makers come from far and wide to experience University of Chicago and Chicago Museum of Science and Industry in South Shore. Stay within walking distance of these fantastic attractions and visit them whenever you please.

How far in advance should I book my South Shore holiday?

Search Expedia to compare international fares as soon as possible. You can usually purchase a seat up to 12 months before departure. If you can't see your preferred air carrier, or you have to book last minute, don't despair. Cheap tickets to South Shore sometimes emerge a few weeks before departure.

What does an Expedia South Shore travel package include?

That depends on what you want. If you're travelling solo, you might decide to combine flights and hotels. Bringing the whole family to South Shore? A travel package including hotels, flights and rental cars might suit you better. Expedia gives you the freedom and flexibility to tailor-make your travel package.

What should I know before booking a South Shore travel package?

You'll save plenty with an Expedia travel package. Bundle your airfares, rental cars and hotels and score fantastic discounts. Hotels aren't your only option, however. We have island resorts, creek-side mountain cabins and even treehouses and ranches!

Can I choose my airline with a South Shore Expedia holiday package?

Expedia has access to more than 550 partner airlines worldwide, so you sure can! Simply select the carrier you want and put together your ideal South Shore holiday.

If I'm not able to travel, can I cancel my South Shore holiday package?

We understand — sometimes life doesn't go according to plan. If you've booked a South Shore holiday package and have to amend or cancel it, we can help. It's always worth checking out our Customer Service Portal first for information. But in general, if you've taken out your package within 24 hours, you may be able to cancel or change your itinerary at no cost. If it's been longer than 24 hours, your airline, hotel or car rental company may impose a charge.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.