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Winthrop Harbor Vacations

Pack those stellar shades. We have Winthrop Harbor 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 Winthrop Harbor – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Winthrop Harbor 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 Winthrop Harbor

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 Winthrop Harbor 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 Winthrop Harbor well.

Top Hotel Deals

See all 94 Hotels in Winthrop Harbor
Sun Inn Motel

Sun Inn Motel

301 Sheridan Road, Winthrop Harbor
3.0 out of 5.0

Situated in Winthrop Harbor, this motel is within 6 mi (10 km) of Keno Drive-In, Illinois Beach State Park, and Jelly Belly Center. Anderson Arts Center and ...

$49

$49
La Villa Motel

La Villa Motel

1401 Sheridan, Winthrop Harbor
2.5 out of 5.0

Situated in Winthrop Harbor, this motel is within 6 mi (10 km) of Illinois Beach State Park, Greenshire Golf Course, and Keno Drive-In. Jack Benny Center for ...

$65

$65
Candlewood Suites Chicago-Waukegan

Candlewood Suites Chicago-Waukegan

1151 S Waukegan Rd, Waukegan
3.0 out of 5.0

Situated in Waukegan, this hotel is within 6 mi (10 km) of Rosalind Franklin University of Medicine and Science, James Lovell Federal Health Care Center, and ...

$68

$68
Super 8 Mundelein/Libertyville Area

Super 8 Mundelein/Libertyville Area

1950 S. Lake St., Mundelein
2.0 out of 5.0

Situated in Mundelein, this motel is 2.9 mi (4.6 km) from Cuneo Mansion and Gardens and within 6 mi (10 km) of Raupp Memorial Museum and Lake County Fairgrounds. ...

$48

$48
Ramada Waukegan/Great Lakes

Ramada Waukegan/Great Lakes

200 N Green Bay Rd, Waukegan
3.5 out of 5.0

Situated in Waukegan, this hotel is 2.6 mi (4.2 km) from Genesee Theater and 3 mi (4.8 km) from Waukegan Harbor. Six Flags Great America and Bonnie Brook Golf ...

$54

$54
Hilton Garden Inn Lake Forest Mettawa

Hilton Garden Inn Lake Forest Mettawa

26225 North Riverwoods Boulevard, Mettawa
3.5 out of 5.0

Situated near the beach, this hotel is 2.9 mi (4.7 km) from Lambs Farm and 3.1 mi (5 km) from Cuneo Mansion and Gardens. Northwestern Lake Forest Hospital and ...

$89

$89
Red Carpet Inn Great Lakes

Red Carpet Inn Great Lakes

3207 Buckley Rd, North Chicago
2.0 out of 5.0

Situated in North Chicago, this hotel is within 3 mi (5 km) of Rosalind Franklin University of Medicine and Science, James Lovell Federal Health Care Center, ...

$53

$53
The Inn at Market Square

The Inn at Market Square

2723 Sheridan Rd, Zion
3.5 out of 5.0

Situated in Zion, this hotel is 1.4 mi (2.3 km) from Illinois Beach State Park and 2.6 mi (4.1 km) from Greenshire Golf Course. Jack Benny Center for the Arts ...

$105

$105
Country Inn & Suites by Radisson, Kenosha, WI

Country Inn & Suites by Radisson, Kenosha, WI

7011 122nd Ave, Kenosha
2.5 out of 5.0

Situated in Kenosha, this hotel is 0.5 mi (0.8 km) from America's Action Territory Family Fun Park and within 6 mi (10 km) of Pleasant Prairie Premium Outlets ...

$87

$87
Wyndham Garden Kenosha Harborside

Wyndham Garden Kenosha Harborside

5125 6th Ave, Kenosha
4.0 out of 5.0

Located in Downtown Kenosha, this hotel is within a 10-minute walk of Kenosha History Center and Alpaca Art. Civil War Museum and Kenosha Public Museum are also ...

$81

$81

Top Flight Deals

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