Chicago Weekend Get-Away

Chicago has a special place in my heart as I lived close by in Illinois a very, very long time ago (between the ages of 6 and 8)…. I have vague memories of going up the John Hancock building and trying to get my head around the fact that Lake Michigan is actually a lake and not a sea, even though it is so big you can’t see across it.

Luckily enough, Inessa from the lovely blog Diaper Style Memoirs offered to write a post for us with a more reliable version of things to do in Chicago. By the way the Chicago sky line is a watercolour & ink drawing by Comic Nurse on Etsy. Isn’t it beautiful?

Here are Inessa’s tips for a weekend with kids in Chicago:

Chicago is truly a special town.  There are so many things to do and see here for the entire family, a weekend isn’t long enough to experience everything this wonderful city has to offer.  But, a weekend is long enough to get a little taste — a taste that will surely have you coming back for more.


Chicago is a great restaurant town with restaurants to please every palette and every budget.  It’s where the deep-dish pizza was invented and where the Chicago style hot dog was born.   Here are just a few of my favorite places you have to try while you’re here.

  • Fine dine at L2O – a splurge is an understatement but the food is out of this world.   Situated in the historic Belden-Stratford hotel, this seafood restaurant is in a league of its own.  The food, the décor, the service and the ambiance are all top notch. L2O is a great restaurant for that extra special occasion.   Don’t forget to bring your camera.  I am sure you will spend half the night just taking pictures of the food.  It is just that gorgeous!
  • Brunch overlooking the city at the Signature Room – located on the 95th floor of the historic Hancock building, this is the only restaurant that serves panoramic views of the city along side your meal.   The service is great and the brunch choices are abundant.  But the best part is – you can sip on your Mimosas while taking in the breathtaking views of the skyline, the beach and the pier.
  • Have chic savory bites at AVEC – a great place to eat with a group.  Avec is a wine bar that offers a menu of rustic food inspired by the wine-growing regions of southern Europe.  The menu is a collection of small dishes that are meant to be shared with fellow diners making the entire dining experience that much more personal and uninhibited.  You really can’t go wrong with anything on the menu but the bacon wrapped dates in piquillo pepper and tomato sauce have most people that try these delectable treats hooked.  So hooked in fact, that they take a cab directly to Avec from O’Hare airport every time they come to Chicago.  But I am not mentioning any names ;).
  • Savor the classic deep dish at Lou Malnati’s – this is the place for deep-dish pizza.   Consistently delicious and family friendly, this restaurant is always packed.  You will understand why when you taste the buttery crust, sweet chunky tomato sauce and fresh homemade sausage.  No other deep-dish compares to a Lou Malnati’s pie.   Arguably, it is the original deep-dish creation.
  • Eat a Chicago style dog at Gene & Judes – this is by far the best Chicago style hot dog in the city.  Well, a little outside the city but it is worth the drive.  Day or night, the line of patrons curves around the corner and then swings back again.   The hot dogs are served Chicago style with onions, relish, mustard and sport peppers.  No ketchup here!  The best part, the mound of fresh cut fries on top!   Be prepared to take your dogs to go.  Standing room only and there is no room to stand.
  • Snack on gourmet popcorn at Garrett Popcorn – a Chicago tradition, this freshly hot-aired popped corn has been the most sought-after popcorn for over 60 years.  Each batch is popped in old-fashioned copper kettles in small batches.  There are a number of flavors to choose from but The CaramelCrisp and the CheeseCorn varieties are my personal favorites.  Oprah’s too.


  • See the animals at the Brookfield Zoo – a short drive from downtown, the Brookfield Zoo is spread across more than 216 acres and houses thousands of animals from around the world.    It is a must trip for any animal lover big and small.   The resident animals live in specially designed, walk through environments so you can view them in their natural settings.  There are many highlights including the Living Coast, which showcases 60 species in recreated waterfalls and ocean depths akin to those of the western coasts of Peru and Chile and the Seven Seas Panorama, the home of the soaring dolphins.
  • Pick out a doll and have some tea at The American Girl Place – a haven for little girls, American Girl Place has everything a little girl can wish for – dolls, books, accessories, three floors of shopping, a photo studio, more dolls, a theatre, a café and yes, even a doll hair salon.
  • Ride the Ferris Wheel and Play Mini Golf at Navy Pier – Navy Pier is Chicago’s lakefront playground.  You can spend the entire day here walking through more than 50 acres of parks, promenades, gardens, shops and attractions.  The kids will love soaring way up high above the city while riding the 150 foot tall Ferris wheel.  There is a merry-go-round for the smaller kiddos and an 18-hole miniature golf course for the entire clan.  If you visit the pier on Wednesdays or Saturdays during the summer months, expect to see a magnificent fireworks display.
  • Learn while playing at the Chicago Children’s Museum – a great place for family-friendly blend of interactive exhibits and innovative educational programs.  Here children can build a dam in WaterWays, create a flying machine in Inventing Lab, enjoy an “outdoor” adventure in Treehouse Trails, build a skyscraper in Skyline, or create collaboratively in daily Kraft Artabounds Studio workshops.
  • Frolic in the water of the Crown Fountain in the summer and skate at the McCormick Tribune Ice Rink during the winter chill – Millennium Park in the heart of downtown Chicago offers visitors a wide range of interactive attractions including outdoor music, art displays, and dining al fresco.  You can’t miss the Crown Fountain with its two tall towers, changing video images of Chicagoan’s faces and cascading water.  Children spend hours during the summer playing in the fountain’s shallow reflecting pool.  The Cloud Gate is another architectural wonder loved by all.  Better known as “The Bean” by the locals, the sculpture has the appearance of a drop of liquid mercury.  Its mirrored surface offers an amazing reflection of the city’s skyline specially on a clear sunny day.
  • Sail on Lake Michigan – during the warmer months you can charter a sailboat and set sail.  This is an amazing way to see the Chicago Skyline.  Sail on Wednesday or Saturday and watch the Navy Pier fireworks explode on the water.  Truly a magical experience.


  • Experience the Chicago from afar  – the best way to see all the amazing skyscrapers and learn about the city’s rich architectural history is by taking a boat tour from Navy Pier.
  • Take in amazing art at the world-renowned Art Institute of Chicago – the museum is located in the heart of the city and houses one of the world’s most notable collection of Impressionist and Post-Impressionist art.   Families will find lots of friendly spaces and inspiring activities.  Kids will have fun creating their own art, visiting exhibitions, participating in special games and playing with Artie the Lion, the Institute’s friendly mascot.
  • See dolphins soar at the Shedd Aquarium and walk with dinosaurs at the Filed Museum – the aquarium is one of the largest in the world with several different exhibits and a 4D theatre and the Field museum is the home of Sue – the most complete T-Rex skeleton.   Both places will provide the little ones with hours of entertainment.
  • Go to a baseball game at US Cellular Field – go to a Crosstown Classic game between the Chicago White Sox and the Cubs and see the rivalry between the north and the south side of the city come to live.  For all the sports fans out there, Chicago is the place to be.  Chicagoans are passionate about their sports and their teams – from the White Sox and the Cubs, to the Bears, the Bulls and the Blackhawks.  Whatever your favorite sport is, Chicago has a way for you to experience the thrill of the game.


  • The Magnificent Mile – you will find everything your little heart desires on Michigan Avenue in the heart of downtown.  From major fashion houses like Chanel to trendy retailers, the Magnificent Mile shops will fulfill everyone’s retail fantasies.
  • Galt Baby & Toys – a great store for the little ones offering unique and innovative products you may not be able to find elsewhere.  Galt offers an extensive selection of strollers, baby gear, furniture and toys.


  • Hotel Sofitel – located on the Magnificent Mile, this European inspired boutique hotel boasts great views of the Chicago skyline and is steps away from all the great shopping on Michigan Avenue.   The little guests receive their own Sofitel teddy bear to take home and indulge in the special kid’s all you can eat dessert table.
  • The Drake Hotel – a historic landmark, this luxury hotel is as fun or kids as it is for adults.  Bathrobes and slippers are supplied for the entire family – big sizes for mom and dad and smaller sizes for the little ones.  There is a turn down service that includes milk and cookies, afternoon tea and even Nintendo.


Comments (6)

April 29, 2011

I lived in Chicago working as an au-pair when I was 23 and I have to say than it is one of my favorite cities in the world. And specially if you are going with kids. As an au-pair and I had to find great places each week to go with the kids to keep them entertaining and Chicago has a great offer for the little ones. I specially love The Children’s Museum, Sheed Aquarium, Navy Pier, Lincoln Park zoo… The Lake…
It is really an incredible city, I’m looking forward to go there again but this time with my own kid ;).
Thanks for this great guide, it brings back old memories 😉
Have a great weekend.

Courtney in London
April 29, 2011

Thanks Inessa for the great guide! I love the way you wrote it — makes me want to go back to Chicago!
xo Courtney

Esther in Amsterdam
April 29, 2011

Oh, I want to go… But will have to do with the print for now… 😉

April 29, 2011

I would like to put a plug for my neighborhood, Wicker Park. There are several children’s play parks, child friendly restaurants and shops. For grown-ups, there are lots of boutiques, live music venues and bars. There is a family friendly bed and breakfast that has two bedroom and three bedroom apartments, Wicker Park Inn.

April 30, 2011

[…] this week’s posts, my contributory posts on Little Miss Heirlooms and Spearmint Baby and my Chicago City Guide guest post on Babycchino Kids, one of my all time favorite blogs! Please don’t forget to cast a vote for […]

May 6, 2011

Great Post Inessa!

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