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Beaches, beef and the Bean: 48 Hours in Chicago

Pizza, beaches and a Billy Goat Tavern.

  • 39
  • 27:42
  • 1,675 mi
  • $278
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Created by LeeChristine - June 25th 2018

Chicago is the Midwest's biggest city, and with its famously tall skyscrapers, notorious mob history, and famously decadent takes on everything from pizza to hot dogs to popcorn, it's definitely the most personality-packed as well. Whether you're sticking to the Magnificent Mile for some high-end, totally luxe shopping, going to Wrigleyville to immerse yourself in the thrill of a Cubs game, or heading out to Logan Square and Wicker Park to hang out with the hipsters, you'll see that there are many sides to Chicago that are all worth exploring.

1046 West Diversey Avenue, Chicago, Illinois, United States

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6mi 00h 13m
Photo of Navy Pier
3.9

700 E Grand Ave, Chicago, IL, US

Navy Pier

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Yes, Navy Pier is touristy...but it's still pretty fun. The massive Ferris Wheel is worth a ride at least once, and it can be nice to stroll past all the vendors hawking tchotchkes and enjoy the breeze and lakeside views. Fun fact: the world's first-ever Ferris Wheel debuted at the 1893 Chicago World's Fair!

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1mi 00h 05m
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0mi 00h 01m
Photo of Millennium Park
4.5

201 E. Randolph St., Chicago, IL, US

Millennium Park

3

When you're ready to work off that sandwich, head to Millennium Park. It's pretty huge, and home to all kinds of Chicago icons. You can't stop by the Windy City without taking a selfie by The Bean (aka Cloud Gate), or visiting the classic fountain. This park pretty much always has something going on, so plan to spend some time exploring.

4
0mi 00h 02m

162 E Superior St, Chicago, IL, US

Gino's East

4

By now hopefully you've worked up a big appetite, because Gino's East makes the best Chicago-style deep dish pizza in the city, and it is, in a word, intense. Nosh on slices of pizza with a rich, buttery cornmeal crust that's filled to the brim with gooey cheese, tomato sauce, and loads of toppings.

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3mi 00h 07m

565 West Jackson Boulevard, Chicago, Illinois, United States

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1mi 00h 04m
Photo of Chicago Architecture Foundation River Cruise aboard Chicago's First Lady Cruises
5.0

Southeast Corner of Michigan and Wacker, Chicago, IL, US

Chicago Architecture Foundation River Cruise aboard Chicago's First Lady Cruises

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2mi 00h 08m

1200 S DuSable Lake Shore, Chicago, IL, US

John G. Shedd Aquarium

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2mi 00h 07m
Photo of The Willis Tower (Sears Tower)
4.5

233 S Wacker Dr, Chicago, IL, US

The Willis Tower (Sears Tower)

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0mi 00h 00m

233 S Wacker Dr, 103rd Floor, Chicago, IL, US

Chicago Skydeck

9

If you're afraid of heights, then you'll maybe want to pass on a trip to the Skydeck. It's located on the 103rd floor of the Willis Tower (better known as the Sears Tower, the tallest building in Chicago, and the Western hemisphere), which offers views stretching 50 miles into 4 states. And if you aren't afraid of heights, then you'll want to step onto The Ledge, a glass-floored box that lets you look straight down!

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5mi 00h 11m

2622 N Clark St, Chicago, IL, US

The Wieners Circle

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For a late-late night drink (we're talking 4 a.m. here), the Wieners Circle is perfect for night owls who are a little bit hungry...that is, if you can handle a side of verbal abuse with your hot dog and fries. The service is quick, the dogs are tasty, and the people-watching is incredible, the servers are famously sassy, and the crowd is often drunk.

951 Chicago Ave, Oak Park, IL, US

Frank Lloyd Wright Home And Studio

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2mi 00h 06m

1046 West Diversey Avenue, Chicago, Illinois, United States

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101mi 01h 44m

Saint Joseph, Michigan, United States

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20mi 00h 25m
Photo of Van Buren State Park
4.7

23960 Ruggles Rd, South Haven, MI, US

Van Buren State Park

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37mi 00h 41m

360 Douglas Ave, Holland, MI, US

DeBoer Bakkerij Restaurant

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5mi 00h 09m

Holland State Park, Holland, Michigan, United States

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Holland, Michigan, United States

11 E 8th St, Holland, MI, US

Crane's In The City

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187mi 02h 54m

The best time of year to have a 48 hour adventure in Chicago: Winters (heck, even early spring and late fall) here can be brutally cold and windy...and it snows quite often, so aim to visit during warmer weather, unless a little chill doesn't bother you. Keep in mind, you'll be using public transportation and walking a bit, so dress appropriately.