How to PLAN a Summer Weekend in Chicago

Categories: Travel

There is NO better city in the Summer anywhere in the country than CHICAGO.  Every summer weekend, people flee NYC like cats doused with a water hose.  In Boston they gun their engines for the Cape, the Vineyard, or Block Island. New Jersey it’s the shore.  But in Chicago, they stay PUT because after a five months of grueling winter they are hell-bent on squeezing the  most out of the gorgeous weather, the beautiful lakefront and the super-fun festivals and activities. Travelling to Chicago in the summer is affordable and a GREAT IDEA.  Here are some IDEAS and INSPIRATION for planning the PERFECT WEEKEND:IMG_09471. Baseball! Check the Cubs and White Sox schedule.  Get tickets to a game.  Few things are more iconic than a beer and a dog at the famed Wrigley Field while hearing the crack of the bat and feeling the hot sun beat down on your face and then you can spend the afternoon after the game exploring the Wrigleyville neighborhood.  Rockit Bar and Grill is great spot for burger after game. The Cubby Bear is the go to post-Cubs game bar…or the place to go if you didn’t get tickets.  And those famous Chicago hot dogs, you can try one at Clark Street Dogs, a six block walk from the stadium.

2. Theatre! Check out the Chicago Theatre schedule as well as the Broadway in Chicago schedule. Motown is playing right now and it is fantastic!

3. Comedy!  How about Zanie’s Comedy club or the famous Second City where Jim Belushi and Tina Fey got their start?  Perfect way to end a night after a great meal out.

Gino’s North in Edgewater

4. Foodie-destination!  Chicago’s food scene is world class and rivals NYC and San Francisco for diversity and talent.  Check out  for Chicago’s hottest restaurants.  If you are not into the uber-trendy, how about some deep-dish pizza at Lou Malnati’s, Pizano’s, Giordano’s, or lesser known Gino’s North in Edgewater known for their amazing THIN crust.  Al Fresco dining is the only way to go in the Summer and restaurants go out of their way to maximize and increase their outdoor seating for Summer-time.,, Here’s a favorite spot on Michigan avenue for drinks and great food…click here.


5. Head to the Beach!  A short walk from your hotel is 28 miles of Lake Michigan beach front and 18 miles of jogging biking trails where you can sit and enjoy the sun and sand and bring a picnic lunch. You can also rent a bike through the city’s bike-renting program and really spend the day exploring.  For more here.   If you want to eat AT the beach both Ohio Street beach and Oak Street beach have sit-down restaurants right off the sand to take in the view and enjoy a drink and a light meal.

6. The Art Institute of Chicago!   One of the finest museums in the country.  Devote an afternoon at least to enjoying it properly. And while you are there plan to eat at Terzo Piano in the Modern Wing of the Art Institute.  The Field Museum, the Museum of Science and Industry and the Adler Planetarium all make great destinations especially with children.  It can be overwhelming to do more than one or two museums a day so I would pick what interests you the most and then shake it up on the other days of your trip.

7. The Shedd Aquarium!  With kids – this is a must-do.  If single or child-less, Wednesday nights offer cocktails and jazz overlooking the spectacular city-skyline. FANTASTIC and a truly unique experience. It’s called Jazzin’ at the Shedd and it is fab!

8. Chicago Symphony!  Maestro Ricardo Muti dazzles audiences with his impressive conducting skills for a night to remember!

9. Festivals!  Check to see if one of Chicago’s many many street festivals is going on the weekend you are here.  My favorite is the Old Town Art Fair where you can grab a glass of sangria and mill around the hundreds of booths filled of original art from all over the country. Well worth the price of admission which is 10 bucks?!  And if you happen to be here the weekend of August 16th, you will be in for a thrill as the Chicago Air and Water Show is going on along the lakefront!

10. Shopping the Magnificent Mile! Michigan Avenue is one of America’s great shopping destination offering one mile of stores to stroll and shop and eat at your leisure.  Oak Street offers smaller boutiques like Tory Burch, Vince, and Kate Spade. Ikram is a nationally reknowned boutique that has had the pleasure of dressing First Lady Michelle Obama. Her exquisite taste is obvious the second you walk in this extremely pricey shopping experience.  If you continue down Rush Street, there are many options for an outdoor lunch like Hugo’s Frog Bar, Tavern on Rush, or Le Colonial.

11. Affordable Hotels!  I would try to stay somewhere along or off of Michigan avenue. There are just too many options to not find one that fits in your budget.  I think the Palmer House Hilton is a gorgeous and historic old hotel that is usually really well priced and very close to the Art Institute and Millennium Park. If you are looking for very trendy, the Thompson Hotel and the Langham are very new and are getting great buzz.

12.  The Bean!  Millenium Park is a great spot to spend the afternoon in between shopping and museum going.  The bean is a mirrored architectural structure that has become an iconic Chicago spot (officially called Cloudgate)….you have to take a selfie with your mirrored selfie behind you!  Touristy for sure but lots of fun!  PicMonkey Collage 2

13. Rooftop Bars! There are plenty around the city but few as stunning as the The Terrace at the gleaming Trump Tower. Come ready to pay handsomely for a well-crafted cocktail, but the atmostphere and the view down the Chicago River can’t be beat.  Fulton’s on the River, Epic, the Wit Hotel are all wonderful for a drink with a view.  Check out this link.. or you can look at my recent post on my FAVORITE spot the J Parker…click here.

14. Architecture!  One of the most distinctive aspects of the city of Chicago is its gorgeous architecture and THE best way to really appreciate and enjoy this is by taking an Architectural Boat Tour.  For 50 dollars you will wind down the Chicago River while a guide gives you the 411 of which building you are looking at and the history of how it came to be.  MUST-DO!!!  Every person who does this says it’s one of their favorite things they did in Chicago!! Be sure to find the boat where you can buy a drink….some do and some don’t.,

15. Neighborhoods! There are more than 200 different neighborhoods that make up the city of Chicago and if you are here for more than a few days you’d be missing out if you didn’t try to hit a few of them to see how each one is so unique and cool.   From the gorgeous murals reflecting the Mexican heritage of Pilsen, to the Swedish American Museum in the once Swedish neighborhood of Andersonville, to the 2 mile stretch of Indian restaurants on Devon Avenue, Chicago’s neighborhoods and former and current ethnic pockets truly tell the story of the “great American city of Chicago.”

16. Jazz!  You cannot miss the incredible venues to watch LIVE JAZZ in Chicago. Whether it’s the iconic Buddy Guy’s Legend’s Bar where the namesake is most likely sitting at the bar talking to an unsuspecting patron, or Kingston Mines where the sets go late into the night and into the early morning, or the Green Mill Jazz bar a little farther Uptown where the old school decor and buzzing vibe once set the scene for Al Capone and his cronies for late night entertainment. or


17.  And finally Views from HIGH Above!  Two of the country’s tallest buildings are in Chicago and they both offer jaw-dropping views of the city and the view below.  Whether you are literally tilting out of the window at the new John Hancock tourist attraction called 360Chicago  or you are teetering out on the glass skydeck at the former Sears now Willis tower, they are both wonderful spots to get your bearings and take in the scope of the country’s second largest urban area.,


  1. Kate, I’m no Chicago expert but I know you started the lust off right with those Cubbies!! A friend told me he toured Chicago by boat which was extremely enjoyable and an outstanding way to view the city… I like your work!!

    Comment by Gary Greenhill on August 6, 2014 at 2:21 am

  2. Kate, I’m no Chicago expert but I know you started the list off right with those Cubbies!! A friend told me he toured Chicago by boat which was extremely enjoyable and an outstanding way to view the city… I like your work!!
    Sorry for the typo.. Big thumbs

    Comment by Gary Greenhill on August 6, 2014 at 2:42 am

  3. Hi, Kate. Lovely website. But I can barely see the text I’m typing. Here are some random ideas.
    * Bike tour c/o Bobby’s Bike Hike.
    * Segway tour.
    * Boat tours from Navy Pier, incl Windy and the Sea Dog.
    * Stroll the financial district on your own and check out the incredible lobbies of the older office buildings (bring a camera!)
    * Walk along the Riverwalk (and give the Trump sign a bronx cheer).
    * Ride the Ferris Wheel on Navy Pier.
    * Map the fountains east of Michigan Ave (in Paris on the Prairie) and visit them all. Buckingham is obvious, but don’t miss Centennial and Aon.
    * And did I mention pizza? Some out of town friends insist on all pizza all the time when here. So try all the big names and pick a fave.
    * Get lost in the Pedway. (OK in the winter).
    * Wait, Wait. See it live. And hope Paula P is on the panel.
    * Pig out at the farmer’s markets on Division and in Lincoln Park on Saturday morning. Close enough you can hit them both.
    * Get in line early for doughnuts at the Vault.
    * Check for free music at Grant Park.
    * Bike Northerly Island.
    * Stroll the gardens at Millennium.
    * Catch the fireworks on Navy Pier on Saturday night from the shore (not the pier) south of the pier.

    These are (a few) of my favorite things.

    Comment by Jim Cieri on August 6, 2014 at 3:56 am

  4. Thanks for the comments!! Jim – I really love your ideas…gotta add music at Grant Park…and of course the doughnuts at the Vault!!

    Comment by Kate Sullivan on August 6, 2014 at 1:53 pm

  5. This was awesome information! Thanks Kate! I love your photos too! Xoxo

    Comment by Ann Randall on September 1, 2014 at 9:54 pm

Your Name...
Your Email...
Secure and Spam free...
Real Time Web Analytics