South Side Kid friendly Vacations

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Flight and Kid friendly hotel deals in South Side

Price found within the past 48 hours. Click for updated prices.
Marriott Marquis Chicago

Marriott Marquis Chicago

Near South Side
CA $968
per person
Sep 25 - Sep 27
found 21 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (1,006 reviews)
The Wheeler Mansion

The Wheeler Mansion

Near South Side
CA $2,531
per person
Oct 3 - Oct 8
found 5 hours ago
Roundtrip non-stop flight included
Victoria (YYJ) to Chicago (ORD)
9.2/10 Wonderful! (5 reviews)
Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago

Near South Side
CA $1,618
per person
Nov 3 - Nov 8
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (1,238 reviews)
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3 Night Kid friendly holidays in South Side

Price found within the past 48 hours. Click for updated prices.
Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago

Near South Side
CA $1,131
per person
Sep 24 - Sep 27
found 2 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (1,238 reviews)
The Wheeler Mansion

The Wheeler Mansion

Near South Side
CA $1,787
per person
Nov 16 - Nov 19
found 3 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (5 reviews)
Marriott Marquis Chicago

Marriott Marquis Chicago

Near South Side
CA $1,956
per person
Nov 16 - Nov 19
found 3 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (1,006 reviews)
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4 Night Kid friendly holidays in South Side

Price found within the past 48 hours. Click for updated prices.
Jaslin Hotel

Jaslin Hotel

Chinatown
CA $1,067
per person
Sep 23 - Sep 27
found 2 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9/10 Wonderful! (1,278 reviews)
Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago

Near South Side
CA $1,637
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip flight included
Detroit (DTT) to Chicago (ORD)
9.2/10 Wonderful! (1,238 reviews)
Best Western Grant Park Hotel

Best Western Grant Park Hotel

Downtown Chicago
CA $1,211
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
8.2/10 Very good! (2,762 reviews)
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Plan the perfect family-friendly vacation in South Side with Expedia

What are some benefits of booking a family-friendly vacation?

Whether it's luxurious or cheap, family vacations in South Side are among the most memorable experiences you'll ever have with your family. It can be a great way to bond and explore new destinations with the people you love most. Plus, it's easy to keep an eye on your little ones without having to worry about how they are with a sitter back home. You may even meet some other families and establish long-lasting friendships.

How can I find the best family-friendly vacations?

Using search filters makes finding the perfect family-friendly vacation easy. You can implement the search filter for family-friendly accommodations specifically, but that's just the beginning. You'll also find search filters for price range along with the desired number of bedrooms, so you can ensure you have enough space for everyone you want to bring to South Side.

Are there cheap family vacations to South Side?

Price varies quite a bit, ranging from to . The price you'll be paying depends on a variety of factors, and you can filter for them all. You can implement a filter for your budget limitations and also remove any 4- and 5-star stays from your search. You can even filter by accommodation type, which can present you with cheap alternatives to what is typically considered standard.

When should I book family-friendly vacation packages?

The right time to book family-friendly vacation packages in South Side depends on what you're looking for. If you're looking to save, booking during least popular month tends to be cheaper compared to the rest of the year, though that's not always a guarantee. Keep in mind that the off-season and the busy season differ from place to place, with family-friendly vacations in Canada being very different compared to options in France and Spain, for example.

Can I book an all-inclusive family vacation in South Side?

Yes, you'll find plenty of all-inclusive family vacation packages for South Side. To see what's available, just select the all-inclusive filter on your search.

How can I book the best family activity vacation?

If you're looking to make the most out of the available activities in South Side, you'll need to consider what your family likes to do. Cater your itinerary to your family's interests, and you'll create memories that you and your kids will hold on to for the rest of your lives whether it's family ski vacations in South Side or something a bit more relaxed.

Can I find luxury family vacations in South Side?

If you're looking for a luxury family vacation to South Side, you can use search filters to find the best options available. Activate the filter for 5-star packages to only see the best of the best. Plus, you'll find a range of first-class flights available to make even the journey there top-of-the-line.

How can I search for family vacation deals?

Finding deals is easy when you take advantage of the array of available search filters. You can set budget limitations and remove 4- and 5-star options from your search. If you don't want to miss out on your favourite amenities, however, you can consider travelling during , which often have lower prices because of the off-season in South Side.

Can I book a family vacation package that is fully refundable?

If you're looking for a fully refundable reservation, you won't have to look far on Expedia. Quite a few properties in South Side are fully refundable. You can search for this feature, but always make sure to check the specific property's policies and requirements before booking.

Why should I book my family trip with Expedia?

When you book with Expedia, you can book your accommodation and your flight together, with some discounts available for doing both at once. Additionally, you may be able to enjoy special discounts with Expedia Rewards that will earn you points you can then put toward discounts for subsequent bookings.

Kid friendly Hotels in South Side

Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago

2233 S Martin Luther King Dr Chicago IL
  • 11 min drive from University of Chicago
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
Hyatt Regency McCormick Place Chicago
Best Western Grant Park Hotel

Best Western Grant Park Hotel

1100 S Michigan Ave Chicago IL
  • 14 min drive from University of Chicago
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms ...
Best Western Grant Park Hotel
Jaslin Hotel

Jaslin Hotel

261 West Cermak Rd Chicago IL
  • 11 min drive from University of Chicago
Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in ...
Jaslin Hotel
See all 469 properties in South Side
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.

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $38
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 $34
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's Lake and River Architecture Tour

Wendella's Lake and River Architecture Tour

CA $63
per adult
94% of travellers recommend
Wendella's Lake and River Architecture Tour
See all activities in South Side

More vacations you might like

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