South Shore Holidays

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Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was €1,367, price is now €1,051 per person
€1,051
per person
21 May - 25 May
found 1 hour ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.8/10 Excellent! (2,096 reviews)
The room was clean, spacious, with good views.

Reviewed on 12 Apr 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was €1,892, price is now €1,374 per person
€1,374
per person
21 May - 25 May
found 1 hour ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (436 reviews)
Overall we enjoyed our stay. A few things that we didn’t care for. One is that the parking was inconvenient due to you having to call to get in every time you leave. Next would be the closet with the furnace was extremely noisy and almost kinda sounding. It came off and on very frequently. Lastly, the bed was as hard as a rock. If you are used a nice bed you can forget it. For the price no thx.

Reviewed on 12 Apr 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was €1,938, price is now €1,544 per person
€1,544
per person
21 May - 25 May
found 1 hour ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,848 reviews)
Beautiful facility, excellent service, professional staff, delicious food!

Reviewed on 7 Apr 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was €1,334, price is now €1,071 per person
€1,071
per person
21 May - 25 May
found 1 hour ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (3,647 reviews)
This hotel far exceeded our expectations! The location was perfect! Parking-easy. Hotel was beautiful and our king suite was wonderful to come back from walking the city to relax. The rooftop had spectacular views and the staff was friendly and helpful. We couldn’t have asked for a better experience!!!!

Reviewed on 11 Apr 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was €1,757, price is now €1,415 per person
€1,415
per person
21 May - 25 May
found 1 hour ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (3,225 reviews)
Booked this hotel because I wanted to enjoy one weekend in Chicago for shopping. I always booked Swissotel because it has rooms that offers river and lake views.

Reviewed on 12 Apr 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 €123 per night from 26 Apr to 27 Apr
€123
26 Apr - 27 Apr
includes taxes & fees
8/10 Very Good! (10,124 reviews)
It needs A LOT of maintenance.

Reviewed on 13 Apr 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 €137 per night from 26 Apr to 27 Apr
€137
26 Apr - 27 Apr
includes taxes & fees
9/10 Wonderful! (4,120 reviews)
Great room

Reviewed on 12 Apr 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 €156 per night from 26 Apr to 27 Apr
€156
26 Apr - 27 Apr
includes taxes & fees
8.6/10 Excellent! (5,850 reviews)
We had a nice stay. Enjoyed breakfast and amenities. Staff were wonderful

Reviewed on 13 Apr 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,485 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.

Frequently asked questions

How much does a South Shore holiday package cost?
Starting from an incredible €1,051, 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.

Popular places to visit

Wrigley Field

Wrigley Field

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

Wrigley Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
Navy Pier

Navy Pier

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

Navy Pier

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

€23
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

€35
per adult
94% of travellers recommend
Art Institute of Chicago
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

€35
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.