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Planning the Perfect Chicago Summer Weekend

Planning the Perfect Chicago Summer Weekend

I’ve been wanting to write this post for a while now and now that it’s summer weather (most days) in Chicago it’s finally the perfect time to share some of my favorite Chicago summer activities.  Some suggestions are tried and true, but I’d like to think that at least a few are ideas that might not appear in a typical google search. Mix and match your favorites for the perfect Chicago summer weekend!

Catch a Cubs Game and Explore Wrigleyville


Catching a Friday day-game and scoring bleacher seats on a hot summer day is one of my all-time favorite Chicago summer activities. Channel you’re inner Ferris Buehler and either play a little hooky from work or schedule your visit accordingly! The food options in and around Wrigley has gotten significantly better over the years but a standard ballpark hot dog, nachos and a cold Old Style are still the way to go. Spend some time exploring Wrigleyville before or after the game; there’s a bar for every flavor although my favorite is Murphy’s Bleachers.

Eat a BYOB Dinner

Chicago has a great variety of BYOB (bring your own booze) establishments and it’s not a complete visit to the city without stopping by one for dinner. Some of my favorites are Chilam Balam, Toro Sushi, Buena Vista Café, Andy’s Thai Kitchen, Angry Crab and Cho Sun Ok.

See a Reggae Show at the Dock at Montrose Beach

While Castaways at North Avenue Beach seems to get all the love, The Dock at Montrose Beach hosts live Reggae shows every Wednesday and has a more laidback vibe.

Enjoy the Lakefront Path


I’ve been lucky enough to live across the street from Chicago’s green lung, Lincoln Park and the lakefront path for the nine years I’ve lived in the city. You could spend an entire day or more walking the 18-mile-long stretch from Edgewater on the North Side to Chicago’s South Shore neighborhood at 71st street where it ends. It passes through dozens of Chicago’s unique neighborhoods and many beaches where you can stop for a drink or bite to eat at Chicago’s lakefront cafes and bars. Castaway’s on North Avenue beach is always a scene in the summer and has a wide choice of frozen alcoholic beverages to help cool you off. Better yet grab a Divvy bike and explore Chicago but don’t forget to dock along the way!

Enjoy Sunday Dim Sum in Chinatown

After our trip through Asia, Jeremy and I decided to make an effort to visit Chinatown for dim sum at least once a month. If you have a car, many of the dim sum restaurants validate your parking for just a couple of bucks. Our favorite restaurants for dim sum are: Phoenix, Triple Crown and MingHin, plus a bonus option on the North-Side called Furama. 

Explore Chicago’s Free Zoo


Spending an hour or two wandering through Lincoln Park Zoo is one of my favorite summer activities. The Zoo is free to everyone, not just city residents and is packed to the gills all summer with family’s trying to catch a glimpse of Chicago’s favorite animals enjoying the sunshine. 

See a Concert at Ravinia


While technically not in the city of Chicago, seeing a show at Ravinia is a must-do for many Chicagoans. This Highland Park music venue boasts a pavilion and huge lawn where you’re free to spend all evening drinking wine and eating all the meats and cheeses while listening to some of the world’s best music acts. In addition, it is the summer home of the Chicago Symphony Orchestra. 

West Side Patio Weather


Chicago’s Northwest side has some of my favorite patios in the whole city with amazing food and drinks. Grab a group of friends or your partner in crime and eat and drink your way through Parson’s Chicken and Fish, Big Star, Best Intentions, Small Cheval and the Moonlighter. Bonus points if you can hop from one to the next using the 606, an elevated trail/park that connects several west-side neighborhoods. Double bonus points if you have time to hop into one of the nearby resale shops in the area so you can purchase some items to blend in with the hipsters.

Millennium and Maggie Daley Park


I couldn’t make a list without including at least one uber-touristy destination because in the end, both parks are actually pretty cool to visit. The Bean is one of Chicago’s most iconic photo spots and I can’t help it that every time in the area I take a selfie with it. Walk around and explore from all different angles so you can get several reflections of the Chicago skyline. Maggie Daley Park has a unique play garden for kids and a climbing wall.

Visit a Street Fest

Chicago is festival crazy all summer long and there is a fest for nearly every neighborhood. Check out Choose Chicago’s fest planner and pick something that appeals to you. Many have live music, food, vendors and local artists. Some of my favorite Chicago fests each year are: Old Town and Wells Street Art Fair, Chicago Blues Fest, Pride Fest, Belmont-Sheffield Music Fest, Taste of Chicago and Randolph Street Fest and Renegade Craft Fair.

Explore Argyle Street

Chicago’s Little Vietnam neighborhood is full of dozens of restaurants with some of the best Vietnam food you can find in the country. Tank Noodle is the popular favorite but really any shop you happen into is bound to have Pho that has been simmering for hours. In the summer on Thursday evenings be sure not to miss their night market with food, music and craft vendors.

Rooftop Weather


Chicago’s rooftops come alive in the summer and they are all perfectly instagrammable; some of the best views in the city can be found at Cindy’s, Noyane and The J Parker. The Eater also has a great list of Chicago’s hottest rooftops. Grab your frozen Rose and strike a pose!

Catch a Movie in the Park

Every year the Chicago Park District turns the city’s parks into accessible cinema for Chicagoans all over the city. You definitely don’t have to be a native to catch a movie and if you’re a traveler on a budget it’s the perfect evening experience to put together your own picnic basket and post up with a blanket for a free flick.

Find Your Favorite Craft Brewery

Chicago is in the midst of a craft beer revolution and new breweries are seemingly popping up every week. There is a brewery for everyone but our favorites are Begyle, Lagunitas, Moody Tongue, Half Acre, On Tour and Off Color. Any brewery that allows dogs are usually at the top of my list! They are literally scattered throughout the whole city so no matter what neighborhood you are in, google is sure to help you find one nearby.

Free Navy Pier Fireworks

Walking Navy Pier and taking a ride on the giant Ferris Wheel is another touristy option, but the real show happens on Wednesday and Saturday evenings when the pier sets off a firework show for the whole city to see. Oh and it’s free!

The Importance of Charitable Ties and Food Events

The Importance of Charitable Ties and Food Events

Keep on Traveling Tony

Keep on Traveling Tony