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Near North Side Vacations

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

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

Top Hotel Deals

See all 120 Hotels in Near North Side
Hotel Felix Chicago

Hotel Felix Chicago

111 W Huron St, Chicago
4.5 out of 5.0

Hotel Felix Chicago is 5 blocks from the Magnificent Mile, one of America’s most dazzling thoroughfares. It’s a 7-minute cab ride to the Navy Pier Ferris Wheel, ...

$63

$63
The Whitehall Hotel

The Whitehall Hotel

105 E Delaware Pl, Chicago
4.0 out of 5.0

Built in 1927, this Chicago hotel is one block from Michigan Avenue shopping and Rush Street restaurants and nightlife; Lake Michigan is within five blocks.

$72

$72
Loews Chicago Hotel

Loews Chicago Hotel

455 North Park Drive, Chicago
5.0 out of 5.0

Located in Near North Side, this luxury hotel is within a 10-minute walk of Tribune Tower and Wrigley Building. Navy Pier and Chicago Children's Museum are also ...

$109

$109
Best Western River North Hotel

Best Western River North Hotel

125 W Ohio St, Chicago
3.0 out of 5.0

Best Western Chicago River North Hotel is centrally located in vibrant downtown, just a few blocks - or a free trolley ride - from the city's landmark Navy Pier ...

$71

$71
Hotel Chicago Downtown, Autograph Collection

Hotel Chicago Downtown, Autograph Collection

333 N Dearborn St, Chicago
4.5 out of 5.0

Located in the heart of downtown Chicago within Marina City, Hotel Chicago Downtown, Autograph Collection, offers guests VIP access to the nearby House of Blues. ...

$89

$89
The Godfrey Hotel Chicago

The Godfrey Hotel Chicago

127 West Huron, at LaSalle, Chicago
5.0 out of 5.0

Located in Near North Side, this spa hotel is within a 15-minute walk of Holy Name Cathedral, John Hancock Center, and Chicago Water Tower. Merchandise Mart ...

$92

$92
Hampton Inn & Suites Chicago Downtown

Hampton Inn & Suites Chicago Downtown

33 West Illinois Street, Chicago
3.5 out of 5.0

The Hampton Inn & Suites Chicago Downtown is a 12-story upscale hotel surrounded by soaring skyscrapers, historic architecture and exciting cultural attractions. ...

$80

$80
DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

300 E Ohio St, Chicago
4.0 out of 5.0

Located in the northern part of downtown, Doubletree Chicago Magnificent Mile is 2 blocks from Magnificent Mile shopping and dining, 3 blocks from Lake Michigan, ...

$74

$74
Embassy Suites Chicago Downtown

Embassy Suites Chicago Downtown

600 N State St, Chicago
3.5 out of 5.0

This 11-story Embassy Suites Chicago Downtown hotel is within a half-mile of Magnificent Mile shopping, the Loop business and theater districts, and the Navy ...

$99

$99
Warwick Allerton - Chicago

Warwick Allerton - Chicago

701 North Michigan Avenue, Chicago
4.5 out of 5.0

Located on Michigan Avenue in the middle of Chicago's Magnificent Mile, this 1920s Italian Renaissance hotel is surrounded by fashionable shops, 1 mile from ...

$72

$72

Top Flight Deals

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