Near South Side Vacation Packages 2025 from $404

Near South Side flight + hotel vacation packages

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

Swissotel - Chicago

Downtown Chicago

Save 100% on your flight

per person

Jul 11 - Jul 14

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features 2 bars/lounges and a 24-hour gym. Traveling on business? Take advantage of the business center, express check-in, and valet parking. A restaurant, a 24-hour front desk, and laundry facilities are also provided.

Hilton Garden Inn Naperville/Warrenville

Save 100% on your flight

per person

Aug 6 - Aug 13

found 16 hours ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Free self parking, a snack bar/deli, and a grocery/convenience store are also offered.

DoubleTree by Hilton Chicago Schaumburg

Save 100% on your flight

per person

Aug 6 - Aug 13

found 16 hours ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy free perks like free self parking and an area shuttle.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

per person

Jul 17 - Jul 21

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.

Radisson Blu Aqua Hotel Chicago

Downtown Chicago

Save 100% on your flight

per person

Aug 20 - Aug 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, express check-out, and valet parking. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and wedding services.

Top Near South Side hotels deals

Congress Plaza Hotel

520 South Michigan Avenue, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$127 nightly

$150 total

Jul 1 - Jul 2

Total includes taxes and fees

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

Reserve now, pay when you stay

$133 nightly

$157 total

Jul 1 - Jul 2

Total includes taxes and fees

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

Reserve now, pay when you stay

$161 nightly

$189 total

Jun 29 - Jun 30

Total includes taxes and fees

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

The Westin Michigan Avenue Chicago

909 North Michigan Ave, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$169 nightly

$198 total

Jun 30 - Jul 1

Total includes taxes and fees

A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the gym, bar/lounge, and coffee shop.

Spa

Pet friendly

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$156 nightly

$183 total

Jun 4 - Jun 5

Total includes taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and valet parking. A coffee shop, a snack bar/deli, and a lobby fireplace are also on offer.

Fairmont Chicago at Millennium Park

200 North Columbus Drive, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$231 nightly

$271 total

Jun 29 - Jun 30

Total includes taxes and fees

A full-service spa, a 24-hour gym, and a restaurant are all featured at this eco-certified hotel. Families will appreciate the onsite laundry facilities and in-room childcare. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi.

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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?

$404 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.