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48 Hours: A Chicago Travel Guide

Last week, I took a "mini" trip from Minneapolis to Chicago for the weekend. While the time flew by way too fast, it was so much getting away for a couple days and exploring the Windy City...and taking lots of photos!

When you travel somewhere for only a day or two, it seems like you want to pack SO many things into your schedule. While I had the best time in Chicago, I have to say it wasn't very hectic, but still really fun. Here's a little peek into how I spent my "48 Hours" in Chicago, and what you could do the next time you go there...

Stay Here

If your brain works like mine (scary, I know) then you're thinking about staying in one of the best hotels in the city since you're travel time is fairly short! Right? Anyway, I stayed at the Trump International Hotel & Tower, and was really happy with my stay. The Trump Tower is located right on the Chicago River and great views of the Navy Pier as well as downtown. It's also super close to Michigan Avenue shopping... score!

The suites in Trump are massive since the building's original purpose was meant for condos.

Other hotels I love: The Peninsula Chicago is darling and The Wit is a super fun hotel with a rooftop lounge and nightclub! (See "Drinks and Dancing" below).


There are so many things to do in Chicago, I can't even list them all! But here are some of my favorites, especially if you're only in town for a day or two... you should be able to check all these off your list!

  • Shop Michigan Ave...obviously! Also known as "The Magnificent Mile"...The vibrant, bustling area is home to upscale shops, luxe fashion outlets, cool restaurants and posh hotels.

  • Check out "The Bean" and get an obligatory reflection photo.

  • Take a photo at the "The Ledge" in the sky deck of the Willis Tower (formerly Sears Tower).

  • Explore the Navy Pier, take a photo of Lake Michigan, and ride the giant ferris wheel.

"The Ledge" transforms how visitors experience Chicago. At 1,353 feet up, The Ledge’s glass boxes extend out 4.3 feet from the skyscraper’s Skydeck on the 103rd floor. Scary!!!

Eat This

If you don't know this about me, I'm REALLY into eating REALLY good food. Chicago's foodie scene is growing so much, and I was able to check out a few super solid spots on my last trip. Here ya go...

The outdoor terrace at Sixteen in the Trump Hotel.

  • Sixteen is a Forbes' Five Star restaurant in the Trump Hotel. Dine with city views offered through 30-foot floor-to-ceiling windows that frame panoramic vistas of Lake Michigan, the Chicago River and the Wrigley Clock Tower. Their outdoor patio is so stunning, and the perfect spot for lunch on those warm, summer days.

  • Hampton Social is a super upbeat, East Coast style restaurant in the River North 'hood (they have 2 new Chicago locations opening this summer). Order a lobster roll and a glass of their famous "Frozé All Day" ...a frozen cocktail containing handmade vodka, rosé, and peach purée. Yummy!

  • Katana is a contemporary, "lounge-y", Japanese comfort food restaurant downtown (super close to Trump Tower). They also have locations in Hollywood and Dubai, so they know what they're doing. I loved the vibe of this restaurant, and will definitely return. All of my food was fantastic, including some faves: truffle edamame, hamachi (best I've ever had!), and the Katana roll.

  • 3 Arts Club Café is located in the Restoration Hardware, or shall I say, "RH Chicago, The Gallery at the Historic Three Arts Club" in the super ritzy Gold Coast neighborhood. The building is filled with dramatic artistic installations featuring renowned designers across the globe, a full-service RH Design Atelier, and a Rooftop Park & Conservatory with sweeping views of the city. I dined in the Grand Courtyard after perusing the "Gallery" (which is 6 floors!) with a glass of bubbly...yum!

Drinks and Dancing

Chicago actually has a pretty fun nightlife! Whether you're looking for a fun happy-hour bar, chic lounge, or rocking nightclub... you'll find something that perfectly fits what you're looking for and I love that! Here are some options...

  • ROOF on the Wit is on the 27th floor of The Wit Hotel, and is particularly a summer hot spot, but always a fun place to visit if you feel like dancing. The rooftop is retractable glass, which is open during the summer--you also get an amazing skyline view of Chicago. There's a DJ on weekends with a super fun dance floor, and also a lounge on the opposite end if you feel like sipping some champagne, ordering a flatbread, and getting some good "people watching" in.

  • Pops for Champagne is a super sleek haunt in River North area, serving up intricate cocktails and, of course, an impressive champagne list (nearly 250 selections!!!). There's also live jazz music most nights. Cute for a date night!

  • Violet Hour is a speakeasy-vibe bar in the heart of Wicker Park. They pride themselves on their unique cocktails and elegant decor. I love their "house rules" ...take a peek in my photo gallery!

Writing this Travel Guide really makes me want to go back to Chicago... I think I'll wait until summertime rolls around. I hope you enjoyed a little slice of this awesome, mid-west city (yay, mid-west!). I highly recommend spending a weekend in Chicago if you've never been there because it's a really easy city to travel to, it's so pretty with a mixture of industrial buildings and Lake Michigan, and there is LOTS to do! Well, until next time... Have a great weekend! I'm going to go plan my next adventure now. Bye!

-Golden Girl

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