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Near West Side Vacations

Pack those stellar shades. We have Near West 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 West Side – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Near West 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 West 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 West 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 West Side well.

Top Hotel Deals

See all 694 Hotels in Near West Side
Hotel Chicago West Loop

Hotel Chicago West Loop

1622 W Jackson Blvd, Chicago
3.0 out of 5.0

Located in Near West Side, this hotel is within 1 mi (2 km) of UIC Pavilion, University of Illinois Chicago, and United Center. Willis Tower and Skydeck Ledge ...

$62

$62
Hampton Inn Chicago West Loop

Hampton Inn Chicago West Loop

116 North Jefferson Street, Chicago
3.0 out of 5.0

Located in Near West Side, this hotel is within a 15-minute walk of Chicago City Hall and Merchandise Mart. Willis Tower and Skydeck Ledge are also within 1 ...

$101

$101
Crowne Plaza Chicago West Loop

Crowne Plaza Chicago West Loop

733 W Madison St, Chicago
4.0 out of 5.0

Just west of the downtown business core, this hotel on Chicago's Near West Side is within a quarter mile of Greektown's restaurants and Harpo Studios. United ...

$108

$108
Chicago Marriott at Medical District/UIC

Chicago Marriott at Medical District/UIC

625 South Ashland Avenue, Chicago
4.0 out of 5.0

Chicago Marriott at Medical District/UIC is a half-mile from United Center and 3 miles from the shopping and dining of Chicago's Magnificent Mile.

$134

$134
Holiday Inn & Suites Chicago - Downtown

Holiday Inn & Suites Chicago - Downtown

506 West Harrison Street, Chicago
3.5 out of 5.0

Located in Near West Side, this hotel is within a 15-minute walk of Willis Tower, Skydeck Ledge, and University of Illinois Chicago. Art Institute of Chicago ...

$80

$80
Ace Hotel Chicago

Ace Hotel Chicago

311 North Morgan Street, Chicago
4.5 out of 5.0

This hotel is located in Chicago (Near West Side), close to Merchandise Mart, Willis Tower, and Skydeck Ledge. Also nearby are University of Illinois Chicago ...

$143

$143
Homewood Suites by Hilton Chicago Downtown West Loop

Homewood Suites by Hilton Chicago Downtown West Loop

118 North Jefferson Street, Chicago
3.5 out of 5.0

Located in Near West Side, this hotel is within a 15-minute walk of Chicago City Hall, Merchandise Mart, and Ford Center for the Performing Arts Oriental Theatre. ...

$134

$134
The Publishing House Bed and Breakfast

The Publishing House Bed and Breakfast

108 N May Street, Chicago
4.0 out of 5.0

This bed & breakfast is located in Chicago (Near West Side), close to United Center.

Handsome 2BR near Restaurant Row by Sonder

Handsome 2BR near Restaurant Row by Sonder

West Randolph Street and Ada Street, Chicago
3.5 out of 5.0

Located in Near West Side, this apartment building is within 1 mi (2 km) of UIC Pavilion and United Center. University of Illinois Chicago and Willis Tower are ...

Smart 2BR near Restaurant Row by Sonder

Smart 2BR near Restaurant Row by Sonder

West Randolph Street and Ada Street, Chicago
4.0 out of 5.0

Located in Near West Side, this apartment building is within 1 mi (2 km) of UIC Pavilion and United Center. University of Illinois Chicago and Willis Tower are ...

Top Flight Deals

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