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Near South Side Vacations

Pack those stellar shades. We have Near South Side vacation deals for you!

If there’s one thing you should spend in this busy world, it’s your vacation days. We know it’s easy to hang onto them, but Hotwire votes for putting them to use. It’s time to let an adventure lead you away from the daily grind. Stock up on what really matters on your trip to Near South Side – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Near South Side vacation packages. Bundling your hotel, car and flight means more unexpected fun with the money you saved. We’ll cover the bases; now it’s time for you to get up and go!

Pack everything you want – then take half of it out

We mean it. It’s far too easy to over-pack. We recommend picking your essentials and washing them along the way. Then you’ll have room for that goofy souvenir you know you want – or for some new outfits from that cute boutique you discover.

Bring comfortable walking shoes on your trip to Near South Side

No one should have to endure walking tours in dress shoes or high heels. No one.

Bring photocopies of your passport or license

You flew home from a great Near South Side vacation but your most important documents stayed behind. We’ve heard that story before and recommend keeping an extra copy on hand – just in case. Hey, at least it wasn’t a family member.

Don’t underestimate the power of earplugs

Among crying babies, rowdy crowds and honking horns, take our word for it. One pair can save you from the zombie-like state of a sleepless night.

Always carry some cash

You’ll be ready for anything from an evil ATM to lost credit cards. Holding a little extra cash in your wallet and carry-on means you can breathe easy if anything unexpected pops up.

Explore like a local

Guidebooks and maps are great for getting an overview of the place, but to really dig in, go where the locals go. Pick up a newspaper or city magazine to see what restaurants and neighborhoods are hot. Check events listings and go see a band or attend a street festival. Or ask your friends for recommendations. You’d be surprised who in your circle knows Near South Side well.

Top Hotel Deals

See all 598 Hotels in Near South Side
Hyatt Regency McCormick Place

Hyatt Regency McCormick Place

2233 S Martin Luther King Dr, Chicago
4.5 out of 5.0

Connected via enclosed skybridge to the McCormick Place convention complex, the Hyatt Regency is adjacent to a Metro station, with easy access to Chicago's downtown ...

$109

$109
Marriott Marquis Chicago

Marriott Marquis Chicago

2121 South Prairie Avenue, Chicago
4.0 out of 5.0

Located in Near South Side, this hotel is within 1 mi (2 km) of McCormick Place, Soldier Field, and Field Museum of Natural History. John G. Shedd Aquarium and ...

$143

$143
Chicago Downtown Condo - Michigan Ave Suite ID #14-15

Chicago Downtown Condo - Michigan Ave Suite ID #14-15

1255 S. Michigan Avenue, Chicago
3.0 out of 5.0

Located in Near South Side, this condo building is within a 15-minute walk of Columbia College Chicago and Grant Park. Art Institute of Chicago and Millennium ...

Furnished Suites in South Loop Chicago

Furnished Suites in South Loop Chicago

1333 S Wabash Ave, Chicago
4.0 out of 5.0

Located in Near South Side, this apartment building is within 1 mi (2 km) of Columbia College Chicago, Art Institute of Chicago, and McCormick Place. Grant Park ...

Stay Alfred Apartments on Wabash

Stay Alfred Apartments on Wabash

1333 S. Wabash Avenue, Chicago
4.5 out of 5.0

This apartment building is located in Chicago (Near South Side), close to Field Museum of Natural History, Soldier Field, and John G. Shedd Aquarium. Also nearby ...

$104

$104
The Wheeler Mansion

The Wheeler Mansion

2020 South Calumet Avenue, Chicago
4.0 out of 5.0

Located in Near South Side, this luxury hotel is within a 10-minute walk of McCormick Place, Glessner House Museum, and Clarke House Museum. National Vietnam ...

$130

$130
Hilton Garden Inn Chicago/mccormick Place, IL

Hilton Garden Inn Chicago/mccormick Place, IL

111 E. Cermak Rd.,, Chicago

This hotel is located in Chicago (Near South Side), close to Wintrust Arena, McCormick Place, and Art Institute of Chicago. Also nearby are Soldier Field and ...

Home2 Suites by Hilton Chicago/mccormick Place, IL

Home2 Suites by Hilton Chicago/mccormick Place, IL

123 E. CERMAK ROAD,, Chicago

This hotel is located in Chicago (Near South Side), close to Wintrust Arena, McCormick Place, and Art Institute of Chicago. Also nearby are Soldier Field and ...

Central Loop Hotel

Central Loop Hotel

111 West Adams Street, Chicago
4.5 out of 5.0

Situated in the heart of "the Loop," the contemporary Central Loop Hotel is steps from all of Chicago’s major business and cultural destinations such as Chicago ...

$76

$76
River Hotel

River Hotel

75 East Wacker Drive, Chicago
4.5 out of 5.0

Located in The Loop, this hotel is within a 10-minute walk of Chicago Theatre, Wrigley Building, and Tribune Tower. Ford Center for the Performing Arts Oriental ...

$68

$68

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.