There’s nothing quite like a summer in Chicago. Brunching al fresco on a patio, heading to the beach for some sand volleyball and sunshine, and dinners and drinks on rooftops are just a few of the reasons why Chicago is a fantastic place to be when the sun comes out. It may be a rough winter, but we make up for it during the summer months. 

I’ve had the pleasure of living here for almost three years and over time have grown a list of favorites that any visitor must try when they’re in town. A perfect weekend in Chicago for a visitor would be to follow this little plan I've laid out, but I've also listed many of my favorites in case you want to make your own itinerary!


Fly in on a Thursday night and plan on flying out late Sunday. Sunday afternoons are so great that you'll want to soak up every minute and get home late... work can always wait! Go to Lou Malnati's on Rush street for Chicago deep dish pizza. You cannot leave without trying it! Lou's is the best but you also can't go wrong with Giordano's, Gino's East or Pizano's. I always recommend knocking this out of the way and it's the best comfort food after a long trip to the Windy City.


Friday morning, wake up early and if you're staying close to the Magnificent Mile. I'd take a stroll up State Street to catch some of the little shops and restaurants and pop over to Michigan Avenue on your way up. One of my favorite areas in the entire city is where Oak Street and Rush Street hit in the Gold Coast. Since the weather should be nice, definitely make your way up to this area for some amazing shopping.

There are a ton of great spots for lunch. If you're looking for something a little nicer, try Le Colonial in the Gold Coast area or pop into Eataly in River North. For the hot dog/beef sandwich lovers out there you will have to make time to go by Portillo's for a true Chicago dog. Post lunch, you need to do something relaxing! Take the architecture tour or the riverboat tour from Wendella or Rocketboats and see the city via the water. It's a must do while you're here - I take all of my visitors at least once! Once that's over, you can easily walk down to The Bean and the Museums from where they drop you off. There's the Art Institute, Shedd Aquarium, and Field Museum all right there. Navy Pier is nearby to check out as well.

After a full day of activities – you’re likely exhausted, so I'd call it a day. Plan ahead for dinner if you want to go pretty much anywhere at a normal time -- OpenTable is your friend! You will not be able to get reservations last minute, so make sure you pick something out early.


Insider's Guide to Chicago

On Saturday, I'd opt for a fun brunch. There are a zillion great places to brunch in the city and especially al fresco. If you'd like to see the city from the highest point, go down to the Willis Tower and stand on the glass ledge - it's a thrill! There are a handful of other tours to try, and if it's the right Saturday - try to catch a Cubs game! They're a blast, even if we don't win.

For dinner, pick another of the many amazing restaurants. Anything on Randolph Street is worth trying to get a reservation for or the handful of restaurants down on Kinzie and Hubbard street. My favorite place to take visitors for cocktails is the John Hancock - you can sip on drinks 90+ floors up and have 360 views of the city. It's absolutely beautiful.


On Sunday, take on the beach and enjoy the sunshine! Stroll through Lincoln Park and even into the neighborhoods over there. You could stop into the J.Parker rooftop for a quick day drink, too, before heading out of the city.

Enjoy this beautiful city and if you haven't been, go book your trip to Chicago now! And for extra help planning your itinerary, check these quick-reference lists of great spots for eating, dining, and doing below.

Insider's Guide to Chicago


  • The Purple Pig
  • Nellcote
  • Little Goat
  • GT Fish and Oyster
  • Bavette’s Bar & Boeuf
  • Summer House Santa Monica
  • Union Sushi + Barbecue
  • Gilt Bar
  • Perennial Virant
  • Prasino
  • Quartino
More options here!

Insider's Guide to Chicago

Insider's Guide to Chicago


  • Drum Bar [rooftop]
  • J. Parker at Hotel Lincoln [rooftop]
  • Little Goat [rooftop]
  • The Pump Room
  • Pops for Champagne
  • Watershed
  • Old Town Pour House
  • The Aviary
  • Violet Hour
  • The Bedford
More options here!


The Bean – a must visit for anyone in town.. snap some great pictures in front of it or with your reflection in it

Hancock Tower – go to the top floor and you’ll get a free, 360 degree view of the city while sipping on cocktails at The Signature Room

Willis Tower (formerly Sears Tower) if you have the time head to the top of the Willis and take the tour to learn interesting facts about Chicago and dare to step out on the Skydeck, the clear ledge that overhangs the city 103 floors up

Navy Pier/River Tour — a must if the weather is nice, they will take you through the architecture and history of the city on the river and depending on the tour will speed up and down the lake for epic views of the skyline, try Wendell or Rocketboat

Lincoln Park/Zoo (it’s free!) – a fun stop that’s easy on the wallet to enjoy the animals or a wonderful stroll through the park

Shedd Aquarium and Field Museum — right next to each other and you can buy a pass for both, the Shedd overlooks the lake with an infinity pool backdrop that is one of the cooler things you’ll see at an Aquarium

Wrigley Field – for those who appreciate references made in the movie Rookie of the Year or who can’t leave the city without a true Chicago hot dog at a Cubs game.. if you have time take the tour!

Oak Street Beach - if you're not looking for a scene from Spring Break and would like to hit the beach, definitely check out Oak Street

Insider's Guide to Chicago


Insider's Guide to Chicago

WHAT TO WEAR:  I would recommend outfits that allow you to easily walk around and are weather permitting. If the weather is warm, I’d suggest a skirt and espadrilles or sandals (if your feet can handle it) or shorts/skirt and a breezy top. When summer starts winding down I’d recommend skinny jeans and a top or sweater and boots. Shoes are key! Chicago is a walking city so make sure you have something comfortable on your feet or you will regret it!

WHEN TO GO:  June – September/October (it will start cooling off in late October, so it depends on what kind of weather you’re looking for!) 

WHERE TO STAY:  I recommend staying north of the River and not in the Loop. It’s most convenient for visitors to find a place somewhat near the Magnificent Mile so that you can do the shopping and sightseeing but still easily get to other parts of the city.

Christine Petric

Christine Petric is the founder of The View From 5 ft. 2, a personal style and fashion blog. Christine provides style tips and inspiration with an additional petite perspective. She is a Texas native that currently resides in Chicago working for Groupon and additionally contributes to the StyleList network. Christine has been spotted in several publications such as, Lucky Magazine, Refinery 29, New York Magazine's The Cut, and Glitter Guide. When she's not blogging, she's exploring the city, learning photography and calligraphy or laughing about something somewhere.

Christine is one of our culture bloggers for The Opener, an exclusive, invite-only contributor network that will bring the best food, culture and innovation writing to the pages of Coca-Cola Journey.