Near South Side Vacation Packages 2025 from $531

Near South Side flight + hotel vacation packages

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

Pendry Chicago

Downtown Chicago

Save 100% on your flight

per person

Jul 10 - Jul 13

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Enjoy the a rooftop terrace and perks like free WiFi. Valet parking, a coffee shop, and a terrace are also offered.

La Banque Hotel

Save 100% on your flight

per person

Jul 12 - Jul 16

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the 24-hour business center. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and concierge services.

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

per person

Jul 10 - Jul 13

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and in-room childcare. Enjoy the gym and perks like free WiFi.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

per person

Jul 10 - Jul 13

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

A restaurant is on site and multilingual staff is available around-the-clock at the 24-hour front desk. Unwind with a drink at one of the 2 bars/lounges and enjoy free perks like buffet breakfast and WiFi in public areas. There's a 24-hour gym on site, and a coffee shop and a snack bar/deli are also provided.

Urban Chicago Oasis

Lakeview

Save 100% on your flight

per person

Jul 10 - Jul 13

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features free WiFi in public areas, laundry facilities, and a virtual front desk.

Top Near South Side hotels deals

Embassy Suites by Hilton Chicago Downtown River North

600 N State St, Chicago, IL

Free Cancellation

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This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and free full breakfast each morning. Valet parking, a business center, and a grocery/convenience store are also offered.

Pool

Breakfast included

Congress Plaza Hotel

520 South Michigan Avenue, Chicago, IL

Free Cancellation

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This smoke-free hotel's 2 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a coffee shop, and a hair salon are also offered.

Free WiFi

Restaurant

citizenM Chicago Downtown

80 East Wacker Place, Chicago, IL

Free Cancellation

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This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A coffee shop, a communal living room, and express check-in are also on offer.

Free WiFi

Restaurant

Hilton Chicago/Magnificent Mile Suites

198 E Delaware Pl, Chicago, IL

Free Cancellation

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A gym, valet parking, and concierge services are featured at this hotel. WiFi in public areas is free. Traveling on business? Take advantage of the 8 conference rooms, business center, and express check-out.

Pet friendly

Free WiFi

Freehand Chicago

19 East Ohio Street, Chicago, IL

Free Cancellation

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This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. Self parking, a coffee shop, and a snack bar/deli are also offered.

Pet friendly

Free WiFi

Hotel Felix River North/Magnificent Mile

111 W Huron St, Chicago, IL

Free Cancellation

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This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A lobby fireplace, a communal living room, and express check-out are also on offer.

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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.

Popular places to visit

McCormick Place

4.5/5(1,805 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

Soldier Field

4.5/5(1,256 reviews)

Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.

Shedd Aquarium

4.5/5(1,675 reviews)

Make time in your itinerary to visit the sea life you'll find at Shedd Aquarium during your visit to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed art scene.

Frequently asked questions

How much are vacation packages to Near South Side?

$531 is all you need to spend for a wonderful vacation in Near South Side. Bundle your flights and hotel into a Travelocity vacation package and watch all the savings add up. With prices as good as these, there’s never been a better time to travel.

Where can I get the best vacation package deals for Near South Side?

For an amazing package deal to Near South Side, no one compares to Travelocity. Pick from as many as 400 partner airlines and 1,000,000 properties around the world to create your ultimate trip — simple as that.

Why should I purchase my Near South Side vacation package via Travelocity?

Fantastic savings, an abundance of thrilling destinations and 24/7 customer service you can rely on — that’s why. And with our Price Match Guarantee, you can rest easy knowing that you’ll always score the best possible deal with Travelocity.

Can I save money on my Near South Side car rental if I bundle it with hotels and flights?

You certainly can — and booking one of our Near South Side vacation packages is the simplest way to do this. Bundle any combination of a hotel, flight, car and tour and land great discounts. The more you bundle, the more you’ll save. There are plenty of top attractions around Near South Side to put on your must-see list, including Six Flags Great America (40 mi from Near South Side). Nothing tops discovering amazing places like this with the freedom of your own rental car.

What is there to do in Near South Side?

Burnham Park is a fantastic place to kick off your sightseeing. Don’t forget your comfy sneakers, because this neighborhood will keep you busy.