Hi Travel Enthusiasts! I’m back with another fun trip to a fantastic city.  This week…the Windy City. Ahhhh, it’s one of my favorite destinations. So much to do, so much to see and it’s an easy flight from home, so there’s no excuse not to visit often. I feel certain this will be my first of many Chicago excursions here on The Traveling Designer. If you are thinking about a weekend get-away there, here is everything you need to know to put together a fabulous two day excursion to Chi-town.

First things first, hotels. I recently had the pleasure of staying at the luxurious Peninsula Hotel for a little anniversary trip with the Hubby. It is spectacular to say the least and with all the hotels wanting to attract guests, you can find some really great deals out there. I think it was the complementary upgrade to a corner suite along with the yummy bottle of red wine and chocolate-dipped strawberries sent up from the concierge that made this one of my favorite hotel experiences ever. And when I hopped on twitter to brag about the service, the Peninsula tweeted right back with a grateful thank-you.  Seriously? All this service and social media too…I’m in love with the Peninsula!

And if the room wasn’t fabulous enough, there is this handsome little bar just off the Peninsula lobby perfect for a martini or a glass of full-bodied red. It’s dark and cozy and a place you want to sit and stay a while, especially when it’s cool outside and you can enjoy the fire. Of course there are some less expensive places to stay in Chicago.  A fun boutique hotel I am fond of is the Raffaello Hotel that is located in this same area of town.

A short walk from the Peninsula is fabulous designer shopping at Branca, the quaint boutique of renown interior designer Alessandra Branca. A feast for the eyes both inside and out, Branca is full of curiosities and collectables and it’s a lovely stop just before lunching at nearby RL.

And if you haven’t already picked it up, you should buy Alessandra’s gorgeous new book, New Classic Interiors.  It is a great read and the photography is gorgeous!

RL, the chic restaurant in the Ralph Lauren flagship store, located just off the corner of Michigan and Chicago Avenues, is a favorite destination of mine for both lunch and dinner.  The scallops I had on my recent trip are quite possibly the best I have ever eaten and the great RL wine list had a plethora of lovely whites to pair with my yummy seafood lunch. You just can’t go wrong with RL.

Conveniently situated across the street is the perfect place to purchase my 5-year-old daughter a souvenir.  And if you happen to bring your little girl with you, afternoon tea is fun in the American Girl cafe.

If you don’t care for hoards of excited young girls, steer clear of this hopping retail establishment. You can instead opt for a visit to the historic Water Tower or head to the top of the John Hancock Tower observatory right next door to see exquisite views of Lake Michigan and downtown Chicago. The Hancock Tower and the other famous Chicago Skyscraper, the Willis Tower (formally known as the Sears Tower), were both designed by the famous architectural firm Skidmore, Owings and Merrill and are major Chicago attractions. If you don’t do heights well, just run over to the Drake Hotel, a few steps away from the Hancock instead, for an afternoon cocktail and a rest of your aching tootsies.

Once your feet are up for more walking, you can hit some of the best shopping in the country all within walking distance down Michigan Avenue.  The magnificent mile has anything and everything that you could want. Some of my favorites destinations include Neiman Marcus, Saks, and the famous corner location of Crate and Barrel.

Just a bit off Michigan Avenue is another great design destination.  The Jonthan Adler store is a feast for the eyes with Jonathan’s inimitable graphic style visible from the front windows.  Loaded with fun gifts that I picked up for my staffers and many things I wanted for myself, I could hardly tear myself away from this cheerful little shop! This funky backgammon set brings back memories of playing with my family as a child and may just come home with me on my next visit.

And when you have had all the shopping you can stand, hop in a cab and head off to the cultural parts of Chicago.  The Chicago Art Institute can keep me busy for hours.  On this most recent trip I was lucky enough to catch the Matisse exhibit.  One of my favorite artists, Matisse’s work was breathtaking in the extraordinary exhibit that was housed just off the new modern wing of the Institute.

And I can never go to the Art Institute without a trip down to the basement to see the Thorne Miniature Rooms. If you are an interiors enthusiast, you just must see the 68 delightful mini versions of historic and modern interior spaces conceived by Mrs. James Ward Thorne and meticulously built by craftsmen of her choosing. There is even a great book that chronicles these fantastic little dollhouse-like versions of rooms.  I can hardly wait until my daughter is old enough to appreciate them so I can take her there.

And a hop, skip and a jump from the Art Institute is the famous Bean at Millennium Park.

What is it about this whimsical chrome sculpture that makes me keep coming back to it?  I can’t depart the Windy city without at least laying my eyes on this shiny bright beauty if only for a second. And by the looks of the crowds that are always there, I am not the only person enamored with it.

There are many historic building worth seeing in Chicago, but it is a new one that has my fancy at the moment. The Elysian hotel is definitely a highlight of Chicago’s new design and architecture scene. The newly opened hotel and residences are a sight to behold. I was lucky enough to get to tour one of the private residences and all I can say is WOW. I felt like Carrie Bradshaw in the Sex and the City movie when Big takes her to the amazing condo and opens the door to reveal glorious windows and phenomenal views.

As if I haven’t already given you enough tips for food and drink, there are great restaurants and bars in the Elysian that are high on the list of chic places to hang out or to see and be seen.

It’s a good thing that I am recommending all this walking in Chicago, because I can’t stop telling you about Chicago’s food. My husband and I met a blogger friend for a casual Chicago pizza lunch at the famous Giordano’s Pizza, conveniently located next door to the Peninsula hotel. I have to say this might have been my first experience with real Chicago style pizza and I was quite impressed.

But don’t eat too much pizza on your next trip because you need to visit another landmark Chicago eatery.  Garrett popcorn is a legend in Chicago and it even made Oprah’s O list.  I have never been there when a crowd wasn’t lined up down the street and around the corner.  But when you get a bite of warm caramel or cheese popcorn (or both) in your mouth, you will decide it was definitely worth the wait.

Art gallery hopping is a great way to walk off some of those popcorn calories. I found a great little art and antiques district on Superior Avenue. I was quite fond of Gallery KH, especially the abstract works of Carolyn Cole.

I fell in love with a pair of citrine yellow murano lamps at Douglas Rosin Antiques.  But don’t worry if you can’t make it to Chicago soon, Douglas Rosin sells their gorgeous wares on 1st dibs.

And no trip to Chicago is complete without dinner at Spiaggia. The favorite restaurant of President and Mrs. Obama might be a bit 80’s in the décor department, but there is nothing dated about the menu.  The food is consistently delicious at this famous Italian eatery thanks to Chef Tony Mantuano. Be sure to get a reservation for your next Chicago visit.

So there you have it. More than enough to keep you busy on your next trip (or three) to Chicago. I hope you will visit some of these well-known and not-so-well-known spots in the Windy City.  I can assure you they will not disappoint.

I’ll be back soon with another exciting adventure from one of my favorite destinations. Until we meet again, Happy Travels!