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Beaches, beef and the Bean: 48 Hours in Chicago

Pizza, beaches and a Billy Goat Tavern.

  • 17

Created by Roadtrippers - April 4th 2016

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.

Mr. Beef On Orleans
4.1

666 N Orleans St, Chicago, IL, US

Mr. Beef On Orleans

One of Chicago's favorite signature dishes is the Italian Beef sandwich, topped with peppers and onions and doused in au jus. Mr. Beef on Orleans has an interesting take on the sandwich, which is flavorful, messy, and a touch spicy.

Millennium Park
4.6

55 N Michigan Ave, Chicago, IL, US

Millennium Park

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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.

Chicago Skydeck
4.5

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

Chicago Skydeck

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!

Gino's East
4.0

162 E Superior St, Chicago, IL, US

Gino's East

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.

Billy Goat Tavern
3.6

600 E Grand Ave, Chicago, IL, US

Billy Goat Tavern

The Billy Goat curse is a huge part of the Chicago Cubs baseball team history, and therefore it's an important part of Chicago history, since the Cubs are so synonymous with the city.

The Billy Goat Tavern was opened by a Chicago local named "Billy Goat" Sianis, so-called because he kept a pet goat. During the 1945 World Series, the Cubs were up on the Detroit Tigers, 2 games to 1. They needed to win two more games at Wrigley Field to nab the title...but during Game Four, Sianis tried to bring his goat into the stadium as a good luck charm, and was told he couldn't. Words were exchanged, and Sianis grew so frustrated that he exclaimed that the Cubs "weren't going to win anymore" as long as the goat wasn't allowed into Wrigley. The Cubs lost that game, and were swept by the Tigers in the rest of the series, losing the championship that they very nearly won.

Sadly (for Cubs fans, at least), Sianis's curse held true for 108 years before the Cubs finally won the World Series. But, even though their tradition of losing has been broken, the Cubs fans' tradition of celebrating wins (and mourning losses) in a pint of Old Style at Sianis's bar will probably always be a tradition.

The Violet Hour
4.6

1520 N Damen Ave, Chicago, IL, US

The Violet Hour

Now for something totally different. Pay tribute to Chicago's gangster past at The Violet Hour, a modern-day speakeasy-inspired bar. Tell the bartender a few words describing your dream drink, and they'll mix something custom just for you!

Slippery Slope
4.0

2357 N Milwaukee Ave, Chicago, IL, US

Slippery Slope

If you're in the mood for a cocktail crawl, head to the Slippery Slope. This is a hipster-y kind of dive, with cocktails and beer served in bottles and cans, which makes it easier to hit the dance floor or play some skeeball downstairs, or take a breather in the lounge upstairs.

Revolution Brewing
4.5

2323 N Milwaukee Ave, Chicago, IL, US

Revolution Brewing

Revolution, Chicago's best-known and biggest craft brewery, serves up 50 different beers each year, ranging from porters to pilsners. Enjoy a beer (or two, or three) at the stunning mahogany bar at the Logan Square brewpub.

2622 N Clark St, Chicago, IL, US

The Wieners Circle

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.

Freehand Chicago
4.0

19 East Ohio Street, Chicago, IL, US

Freehand Chicago

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A hostel? While staying in Chicago? Trust us on this one. The Freehand is outstanding. Book one of the private rooms in this converted 1920's building and you'll be so busy oogling the chic decor, and appreciating the primo location, and savoring meals and drinks at the hip bar and cafe, that you'll forget how cheap the rooms are.

The Publican
4.5

837 W Fulton Market, Chicago, IL, US

The Publican

With a variety of brunch-themed drinks and one of the most refined brunch menus around, The Publican is guaranteed to impress. Red wine poached eggs, smoked pork shoulder over grits, and Meyer lemon donuts are just a sample of delicious delicacies you could enjoy here.

Oak Street Beach
3.7

1001 North Lake Shore Drive, Chicago, IL, US

Oak Street Beach

One of the reasons Chicago is the greatest city in the Midwest? Beaches! The Oak Street Beach, on the shores of Lake Michigan, offers amazing views of the city skyline and views out into the water as well. It's free, and a lot cleaner and less crowded than a seaside beach, so remember towels and swimsuits so you can soak up the sun.

Old Town Social
4.0

455 W North Ave, Chicago, IL, US

Old Town Social

"Upscale sports bar" is how Old Town Social is described, and since Chicago is a town that loves its sports, its worth stopping by here. Start off your meal with an order of house-made mini hot dogs (Chicago-style, of course) and add a burger or sandwich, and a beer to top it all off.

Navy Pier
3.5

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!

John Hancock Observatory
4.6

875 N Michigan Ave, Chicago, IL, US

John Hancock Observatory

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If you thought the view from the Skydeck was terrifyingly awesome, wait until you see what Chicago's other iconically tall skyscraper, 360 Chicago (better known as the John Hancock Observatory) has to offer: Tilt, which leans tourists out at an angle 1,000 feet above the Magnificent Mile. If that's too much, enjoy the panoramic views of the city safely from other spots on the 94th floor.

Harry Caray’s
4.0

33 W Kinzie St, Chicago, IL, US

Harry Caray’s

Just as Harry Caray was a beloved Chicago icon, as an announcer for the Chicago Cubs, Harry Caray's Steakhouse is a classically Chicago institution. It doesn't get any more old-school Midwest than a classic steak dinner in a restaurant done up in sports memorabilia.

Green Mill Jazz Club
4.7

4802 N. Broadway Ave, Chicago, IL, US

Green Mill Jazz Club

Rounding out your 48 hours in Chicago, trust us, a trip uptown to visit the Green Mill is totally worth it. The place is loaded with history. Where else in the world can you sit in Al Capone's favorite booth and listen to live jazz or big band music, or a quirky poetry slam?

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.

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