48 Hours in Chicago | Where to Eat, Sleep, & Play When You Visit Chicago

The Bean

If the Windy City has been on your bucket list for a while, you are in good company. Visiting Chicago has been one of my most memorable and enriching travel experiences, and I’m counting down the days until I can visit again. Chicago is vibrant, social, and full of amazing experiences to try. Explore Chicago by day and discover art, culture, and award winning fare. Paint the town red at night, and Chicago will unfold a treasure trove of jaw dropping views, belly laughs, and nightlife that will make you forget what time it is. If you are looking at making the most of Chicago for a quick visit, consider this 48 hour itenerary for your Chi-town getaway.

Where to Eat, Sleep, & Play

When You Visit Chicago

Kimpton Hotel Allegro Lobby

Where to Stay

If you’re looking for a chic boutique hotel conveniently located in downtown Chicago, look no further than the Kimpton Hotel Allegro. Hotel Allegro is walking distance to the river and Millennium Park and surrounded by ample shopping and great eats. There are plenty of Instagram-able corners located throughout this retro Art Deco inspired hotel, and guests are welcome to gather every evening for Kimpton’s signature happy hour. I found this location ideal, and the chic atmosphere had me inspired to do a photoshoot every time we turned a corner.

Bonus! The hotel is attached to a Starbucks ensuring your morning latte is easy to find.

The Second City Comedy Club


Chicago is known for it’s exceptional theatre scene. Don’t visit the windy city without grabbing tickets to one of it’s famous resident shows, or a touring concert. Chicago is also famed for it’s comedy scene, so make sure to hit up one of the local favorites such as The Second City Comedy Club to catch a rising star in action, or a pop up guest appearance by one of your favorites.

Tip – Many of the Chicago theatres have older architecture. Read the fine print on your ticket carefully and watch out for “obstructed views” these are support poles located throughout the theatre and they will block your view.

A View From the Top

Chicago is full of endless views to feast your eyes on. If you’re looking for the ideal “Bird’s Eye” view, you’ll find it at The Signature Lounge on the 96th. The Signature Lounge is a bit more accessible than it’s sister restaurant The Signature Room on the 95th. No reservation required, just be prepared to wait in line a bit to reach the top. Enjoy light apps and classic cocktails with a view worth a million bucks. Be prepared for crowds, and plenty of tourists trying to catch a photo with the view. I recommend going on an off hour to avoid the larger crowds. Head there mid-week for the night time view or during lunch if you don’t need the after dark ambiance. Note that The Signature Lounge does not take reservations, or allow children under 21 access after 7pm.

Tip- Beware of lines to get to the top (and back to the ground). Also, be prepared to pay premium dollars for the food and cocktails. Insiders secret: The best unobstructed view to grab a picture with is actually in the ladies bathroom (sorry boys).

Late Nights

A visit to Chicago should always include at least one late night out at the club! Disco Chicago pays homage to the glitz and glamour of the 70s disco movement. The wall to wall light up LED floor and non-stop disco tunes transport you to a bygone era where anything goes. Disco is located on Hubbard street which is lined with great clubs to dance the night away in, just be prepared to wait your turn if you are bouncing around, or find a local who knows somebody to bypass the lines. (Tipping the bouncer can’t hurt either!)

Tip – It’s ideal to RSVP online to gain entry through the guest list. Otherwise you’ll be lined up outside waiting your possible turn. Don’t be afraid to wear your favorite 70s attire!  If you do happen to get stuck in line, dressing the part could help your chances to get in.

Charcuterie at Eataly

Good Eats

Everyone wants to know where to find the best eats in Chicago. You could write 40 blogs on food in Chicago, so I’ll just cover the highlight of our trip that packed the biggest punch. Eataly Chicago joins locations in NYC, Boston, LA, and Las Vegas as a premier Italian market and foodie destination. Shop for your favorite cooking gadgets and imported Italian ingredients, sip on espresso, or nosh on charcuterie with a glass of red wine. There is so much to see and enjoy at Eataly, you could easily spend half a day browsing and tasting it’s treasures.

Tip– Come hungry. You’ll want to try one of everything!

The Bean

Local Icon

Perhaps one of the most famous “must-see” attractions in Chicago is Cloud Gate, more commonly known as The Bean. Located in Millennium Park steps away from great food and shopping on Michigan Avenue, The Bean showcases the Chicago skyline in a unique way that begs to be captured on camera. Get creative with your selfies and make sure to explore all sides, and underneath The Bean for an immersive experience that will spark your imagination. Access to The Bean is completely free, so don’t miss this iconic attraction.

Tip– For another unique view of The Bean in the cold season, head to the ice rink below for a memorable experience.

Art Institute of Chicago

Art Institute of Chicago

Immerse yourself in art culture at the Art Institute of Chicago. As one of the oldest and largest art museums in the United States, you’ll be inspired by works of both Contemporary and Modern Art. You could easily spend an entire day steeped in famous masterpieces and historical treasures, so plan accordingly. Highlights of our visit included seeing amazing Impressionist work by Monet, Renoir, and Manet as well as “not to miss” famous works in the museum’s collection including Night Hawks, American Gothic, and A Sunday on La Grande Jatte.

Tip– For great savings consider purchasing a Chicago City Pass which includes admission to great attractions like The Art Institute of Chicago, the Shedd Aquarium, and Skydeck Chicago.


How to fit it all in?

Here’s an Example Itenerary

First Day

9am Arrive in Chicago

12pm Check your bags at your hotel

2pm Grab a matinee at the Theatre

5pm Sunset Drinks at The Signature Lounge

7pm Head to The Second City for the early show

10pm Grab a cocktail then head to Disco for the night

Second Day 

Sleep in

12pm Head to Eataly for brunch

2pm Visit The Bean

3pm Peruse the Art Institute of Chicago

6pm Head to the airport and fly home.


I look forward to hearing all about your adventures when you visit Chicago. If you discover some local treasures that need sharing, please feel free to leave a comment below.

Until then…

Enjoy the Journey!

xo- Amy West


Where to Eat, Sleep, & Play when you Visit Chicago