South Shore Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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

Top Holiday Package Deals in South Shore

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 CA $1,389, price is now CA $921 per person
CA $921
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
Clean room, walkable & quiet. Enjoyed my entire stay.

Reviewed on Jul 9, 2026

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
Downtown Chicago
Price was CA $3,926, price is now CA $2,363 per person
CA $2,363
per person
Sep 20 - Sep 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
I liked everything except that the air conditioner in the hotel hallway was too cold

Reviewed on Jul 8, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $2,047, price is now CA $1,235 per person
CA $1,235
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)
Front desk staff was super helpful and enthusiastic. Smooth check-in, and checkout.

Reviewed on Jul 8, 2026

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Price was CA $2,110, price is now CA $1,436 per person
CA $1,436
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (1,819 reviews)
The room was amazing! It was spacious and clean. The staff were helpful and very considerate. The hotel is located in an ideal location, right off of Michigan Avenue, in the heart of downtown. Shopping and restaurants are within short walking distances.

Reviewed on Jul 8, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $2,153, price is now CA $1,484 per person
CA $1,484
per person
Sep 20 - Sep 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,136 reviews)
Mediocre all around and for the price point not worth it. Great location. But nothing else compelling. Food was only ok. Service was only ok. Nothing memorable. Will seek somewhere else next time.

Reviewed on Jul 8, 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

South Shore Hotel Deals

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 CA $305 per night from Aug 9 to Aug 10
CA $305
CA $410 total
Aug 9 - Aug 10
includes taxes & fees
9.2/10 Wonderful! (1,884 reviews)
"The room was amazing! It was spacious and clean. The staff were helpful and very considerate. The hotel is located in an ideal location, right off of Michigan Avenue, in the heart of downtown. Shopping and restaurants are within short walking distances."

Reviewed on Jul 8, 2026

Omni Chicago Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $204 per night from Jul 27 to Jul 28
CA $204
CA $242 total
Jul 27 - Jul 28
includes taxes & fees
8.2/10 Very good! (1,720 reviews)
"Great time"

Reviewed on Jul 9, 2026

The Chicago Hotel Collection Ambassador Gold Coast
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 CA $263 per night from Aug 6 to Aug 7
CA $263
CA $312 total
Aug 6 - Aug 7
includes taxes & fees
8/10 Very good! (10,208 reviews)
"I was freezing and they were super gracious and got me TWO blankets."

Reviewed on Jul 9, 2026

Congress Plaza Hotel
See all 4,226 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 Vacations
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Frequently asked questions

How much does a South Shore vacation package cost?
Starting from an incredible CA $921, 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 vacation 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?
Vacationers 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 vacation?
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 traveling 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 vacation 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 vacation.
If I'm not able to travel, can I cancel my South Shore vacation package?
We understand — sometimes life doesn't go according to plan. If you've booked a South Shore vacation 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.

Stay near popular South Shore attractions

Stony Island Arts Bank

You can spend time exploring the galleries in Stony Island Arts Bank 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

CA $31
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

CA $35
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's Lake and River Architecture Tour

Wendella's Lake and River Architecture Tour

CA $64
per adult
94% of travellers recommend
Wendella's Lake and 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.