Home Lifestyle Weekend Getaway Idea: Chicago, Illinois

Weekend Getaway Idea: Chicago, Illinois

by Jennifer Tripucka
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This week in our travel series we’re paying a visit to Chicago, Illinois. While the Midwest city is famous for numerous touristy things including Wrigley Field, Magnificent Mile, and obviously, The Bean, there are plenty more to check out that have yet to become mainstream. From the Insta-famous brunch spot that attracts people for its pretty-in-pink “Rosé All day” wall to taking a stroll along the Navy Pier to eat, shop, and play, you’re about to have a jam-packed weekend in one of the most hip Midwest cities around. Hold on tight — here’s your adventure in the Windy City with our weekend getaway to Chicago, Illinois ideas.



Plane Flights

First step: hop in an Uber to Newark Airport {EWR} for a flight to Chicago {ORD}. United offers direct flights to Chi Town, and that’s definitely the best option so you can spend more time exploring. Southwest also offers cheaper flights to Midway, but there’s no assigned seating, FYI.

Hotel Picks

Kinzie Hotel {Boutique Style]



Located in the heart of downtown Chicago, the Kinzie Hotel is the place to stay if you’re all about chic, unique stays. The breathtaking city views from your room combined with luxury amenities and high style just might convince you to stay inside. It’s also rated the pet-friendliest hotel in River North, so you don’t have to worry about getting a pet sitter while you’re away.

The Peninsula Chicago {Five-Star Hotel}



If you’re looking to be waited on hand and foot, the Peninsula Chicago will do just that. The hotel is known for its traditional Asian service, where hospitality is the heart of your stay. Bonus: it ranks #1 among all Illinois hotels participating in the Clean the World Foundation and there’s even a “pint-sized brunch,” where the kids can join in on the adults’ favorite weekend ritual.

The Alise Chicago {Luxurious + Fruity Decor}



At the Alise Chicago, you’ll be welcomed with an oversized pineapple, and we can’t think of anything more IG-worthy than that. Located in the Loop District, you’ll be within walking distance to all the attractions including Millennium Park and the theatre district, where you can catch an award-winning show {CHICAGO, anyone?}. Convenience at its finest {and fruitiest}.

Sofitel Chicago Magnificent Mile {Design Goals}



Got a thing for French architecture? Then you’ll want to lodge at the Sofitel Chicago Magnificent Mile, which is a true gem when it comes to its design — you know that it’s the real deal considering skyscrapers were created in Chi Town. You’ll get views on views of Lake Michigan and the Chicago skyline. You can’t get better than that.

Places to Eat and Drink

Giordano’s or Lombardi’s {Deep Dish Pizza}



Warning: food baby ahead. But it’s totally worth it to experience the widely popular restaurant that dishes up authentic, out-of-this world deep dish pizza. There’s multiple locations {and some in other states now, too} and you can also have frozen pizzas delivered to your home after your trip when you’re really missing the Windy City.

The Hampton Social {Upscale Beachy Restaurant}



When you walk into The Hampton Social, you’ll immediately feel like you’re at the Hamptons. There’s tasteful, nautical decor, live acoustic music during brunch, hammocks, and more details that create a relaxing, vacation-like atmosphere. Oh, and you didn’t really go here if you didn’t snap a pic in front of the rosé all day wall.

Public House {French Fries/Cake Milkshakes

Can’t decide what dessert to eat? Problem solved with the cake shake, where you literally get a piece of cake on top of your deliciously life-changing milkshake that will look amazing in all those Instagram pics. Public House also has some tasty french fries, as if your inner foodie isn’t already leaping for joy.

Asado Coffee Company {Roasts Beans In Shop}



Forget going to a quick-fix coffee shop because at Asado, the beans are actually roasted in the shop. If you’re a so-called coffee snob, you really can’t go anywhere else — especially with such an adorable “coffee” sign outside. This is definitely worth the Uber.

Left Coast {Açai Bowl/Smoothies}



Between the deep-dish pizza and other fattening food, there comes a time where you need an acai bowl — STAT. Get your health fix at Left Coast, which is an adorable, California-inspired quick food spot for healthy eats.

Places to Go Out/Have Cocktails

Three Dots and a Dash {Hawaiian Bar}



Chicago locals head to Three Dots and a Dash on the reg, and we can see why. They’ve got crazy concoctions that will instantly take you away to the tropics even in the most miserable weather. With Hawaiian-themed drinks, complete with gorg toppings, you’re sure to have a blast here.

The Signature Room at 95th {#Views}



Located inside Hancock Tower, 95th offers some prime views while you’re grabbing a drink or eating dinner. This is definitely more of a splurge-worthy occasion, but even the bathrooms have views, so you can’t pass this place up.

Cindy’s Rooftop {Rooftop Bar}



You can NEVER have too many rooftop bars. This one has a green-filled panorama {during the spring and summer, of course}, where you’ll get a spot-on view of all the tourists at The Bean and the water.

Sightseeing MUSTS

Millennium Park/The Bean 


Like many touristy spots, we don’t really have to explain too much about why you’d want to come here. You’ll get an amazing, reflective photo that you can’t get anywhere else.

Navy Pier



Weather you want to shop, dine {Giordano’s is another famous deep-dish pizza place to try here}, or ride the ferris wheel, the Navy Pier offers up something for everyone. It’s perfect for walking off that pizza or enjoying the nice breeze that’s always a guarantee in The Windy City.

Wrigley Field 



Take the group out to the ball game at the iconic Wrigley Field, where you can enjoy some fun in the sun and America’s favorite sport. And with the Cubs’ recent World Series Win, it makes a visit to the park that much more memorable.

Skydeck Chicago



If you’re afraid of heights, this probably isn’t for you, but we suggest putting on a coat of bravery for this one because you won’t regret it. The clear floor allows you to see down below and from all sides, and it’s the scariest, yet coolest feeling in the world. Also, it makes for amazing group photos.

HG Insider Tips

Buy a GoPASS to save serious cash on attractions. An adult pass costs $100 and gets you into the top touristy things like The Shedd Aquarium for nine consecutive days. 

Like NYC, don’t visit when it’s cold. Sure, those pics of you bundled up in a puffer coat and beanie may be adorable, but there’s a ton of misery behind the scenes. 

Don’t buy Cubs tickets in advance. Typically, there are a ton of tickets left over, so you can get ultra cheap tickets at the door. 

Never taken an Uber? Use the promo code HGTAKE20 to get your first ride free here (up to $20).

So there you have it; a quick trip to Chicago, which can be done in a few days, max 5 hours of travel time from Hoboken to Chicago {start-to-finish}.  This post was sponsored by Uber, but having just visited The Windy City, know that we’d never steer you {no pun intended} wrong!

Let us know where we should cover next in our #HobokenTravels!



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