Near South Side Vacation Packages 2025/2026 from $372

Near South Side flight + hotel vacation packages

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

Baymont by Wyndham Chicago/Alsip

Save 100% on your flight

$372

per person

Oct 8 - Oct 14

found 23 hours ago

Roundtrip flight included

Atlanta (ATL) to Chicago (MDW)

This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling for business? Take advantage of the 24-hour business center, express check-out, and conference space. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.

La Banque Hotel

Save 100% on your flight

$533

per person

Oct 13 - Oct 18

found 1 day ago

Roundtrip flight included

Dallas (DFW) 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.

The French Country Inn Lake Geneva

$546

per person

Nov 26 - Nov 30

found 11 hours ago

Roundtrip flight included

Houston (IAH) to Chicago (ORD)

A private beach and a restaurant are featured at this smoke-free hotel. Guests will appreciate free perks like free self parking and WiFi in public areas. A picnic area, luggage storage, and concierge services are also on offer.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$705

per person

Nov 25 - Nov 30

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features 2 bars/lounges and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy a meal from the restaurant and free buffet breakfast each morning.

Hilton Garden Inn Chicago Downtown/Magnificent Mile

Downtown Chicago

Save 100% on your flight

$409

per person

Oct 3 - Oct 6

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and perks like free WiFi. Express check-out, luggage storage, and concierge services are also on offer.

Top Near South Side hotels deals

Congress Plaza Hotel

520 South Michigan Avenue, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$162 nightly

$190 total

Sep 4 - Sep 5

Total with 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

Embassy Suites by Hilton Chicago Downtown River North

600 N State St, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$179 nightly

$210 total

Sep 3 - Sep 4

Total with taxes and fees

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

The Wade

644 N Lake Shore Dr, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$167 nightly

$196 total

Sep 22 - Sep 23

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a 24-hour gym on site, and a 24-hour front desk and express check-in are also provided.

Pool

Pet friendly

Hilton Garden Inn Chicago Downtown/Magnificent Mile

10 E Grand Ave, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$169 nightly

$198 total

Sep 3 - Sep 4

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and perks like free WiFi. Express check-out, luggage storage, and concierge services are also on offer.

Pool

Pet friendly

Hilton Chicago/Magnificent Mile Suites

198 E Delaware Pl, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$161 nightly

$189 total

Sep 22 - Sep 23

Total with 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

citizenM Chicago Downtown

80 East Wacker Place, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$144 nightly

$169 total

Sep 4 - Sep 5

Total with 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

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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 theater scene.

Frequently asked questions

How much are vacation packages to Near South Side?

$372 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.