22 Bloggers Share Chicago’s Must-See Summer Experiences

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There is still a lot of summer left! Late summer and early fall still give you plenty of time to get out and see what Chicago truly has to offer.

From unbelievable sites to unforgettable meals, we asked some of the web’s most trusted travel bloggers to give us their Chicago must-see list for the summer.

Here’s what they recommend.

1.Fireworks Over the Lake


Warm summer nights provide Chicago with the perfect weather to enjoy fantastic displays of fireworks. Different holidays, festivals and events celebrate with explosions of color that bloom across the night sky.

“I want to see the fireworks over Lake Michigan. It is something that I try to see at least once every summer.”  – Kit Graham

Kit Graham is the blogger behind The Kitchen, the author of The Gourmet Grilled Cheese Cookbook, and a co-founder of the Windy City Blogger Collective.

2. Bike ride along the lake to a patio.

The Windy City can’t wait to see you outdoors this summer. Chicago features great bike paths along the water, leading to great outdoor patios with delicious food and beverages.

“Chicago is the best in the summer, so anything outdoors! My favorite things to do are bike ride along our huge lakefront and enjoy a cold beer in one of our many outdoor patios or rooftop bars.”- Lisa Lubin

Lisa Lubin is an established travel/food writer, three-time Emmy®-award winning TV producer, video consultant, and travel industry expert. After more than a decade in broadcast television she took a sabbatical, which turned into three years traveling around the world. She documents her (mis)adventures on her blog, LLworldtour.com. Her writing and photography has been published by American Way Magazine, Wall Street Journal, Chicago Tribune, West Jet Magazine, Sheridan Road Magazine, Smithsonian, the Malibu Times, Encyclopedia Britannica, Orbitz, MapQuest, Jetsetter.com, and Huffington Post. She recently published The Ultimate Travel Tips: Essential Advice for Your Adventures available on Amazon.

After surviving my first Chicago winter, it’s magic to see all of Chicago come to life and embrace the warm weather. Summer in Chicago means bike rides along the lakefront, warm nights out on the town, brunch on a patio, and drinks on a rooftop. My only goal this summer is to be inside as little as possible, so that I can soak up the atmosphere in a city that celebrates every chance it gets!” – Phoebe Blyth

Phoebe has been chasing adventures for as long as she can remember, thanks to growing up in a family who loved travel, adrenaline sports, and the outdoors. She is currently living in Chicago, scratching her itchy feet by running the travel website Many Many Adventures with her other half, Ronnie. She is unable to reconcile her need to travel with her intense desire to adopt a puppy.

3. Paddling for the best view of Chicago’s skyline.

Chicago River

During the summer, one of the best vantage points to take in the impressive skyline is from the Chicago River. From a distance, it’s easier to appreciate the world-class architecture of Chicago.

“The one thing I would like to do in Chicago this summer is to canoe the Chicago River. Everyone speculates where the best vantage point to view the beautiful Chicago skyline is. For me this is a no-brainer. The best view of the Chicago skyline is from a canoe on the Chicago River paddling up from the south.” – Ted Nelson

Ted Nelson is an outdoor adventure travel writer and blogger behind Traveling Ted, which is a website that chronicles his adventures hiking, canoeing, and skiing in the United States and around the world. He also enjoys the cultural side of travel including learning and meeting people from around the world, eating their food, and learning about their history. My goal is to inspire others to travel and provide tips for those who want to follow in my footsteps.

4. Rooftop Drinks


Sometimes, the beautiful buildings of Chicago are best enjoyed from the top while imbibing on fine cocktails. Hopping from one rooftop bar to another gives you a series of great views of the city.

“One of my goals this summer was to get up on some rooftops. Most of us, after work, just head to the closest or our regular watering hole. I decided to branch out. I created a list and got some friends together and we rooftop-hopped one night. Now it wasn’t exactly cheap but it was fun! My website is about living well and spending less in Chicago. The philosophy is: if you save money in all areas of your life all the time then you are able to afford to splurge on pricey cocktails up on rooftops while enjoying the views of our beautiful city. A couple friends read my post about it and now I’m planning another outing!”- Carol Cavazos

Carol Cavazos, a long-time resident of Chicago, is a lifelong frugal living enthusiast. Her website Chicago on the Cheap publishes all the best quality free and cheap activities, daily deals, discount dining and theater tickets. She also shares frugal living tips so you can free up more cash to build wealth while still enjoying life.

5.Taste of Chicago

The sheer amount and variety of fantastic cuisine that Chicago has to offer foodies is one of the main reasons people visit. The Taste of Chicago event is one of the biggest food festivals, taking place annually in Grant Park.

“One of my favorite activities to do in Chicago during the summer is to attend the Taste of Chicago. I always have such an amazing time meeting new people and trying different food from across the city.”  – Raijean Stroud

Raijean Stroud is a fashion, beauty & lifestyle blogger based in Chicago and founder of Swa-Rai.com and Bleeding Heart Project. Launched in 2010, Swa-Rai reports the latest trends in fashion, beauty and lifestyle experiences which includes: entertainment, travel, tech, family, dining and so much more! When not in Chicago, Raijean can be found traveling around the country covering some of the hottest events!

6. Crown Fountain at Millennium Park


During a hot afternoon, taking the family to Crown Fountain in Millennium Park is a great way to cool off for the entire gang. Kids love splashing and chasing each other around the fountain.

“Splash and play at Crown Fountain in Millennium Park! There is nothing better on a hot summer Chicago day than watching my 4-year old son chase the kids back and forth to try and be the first under the spitting fountains to get soaked.”- Sarah Stopek Hirsch

Sarah Stopek Hirsch is an award-winning female entrepreneur and the founder of WellTraveledKids.com. Sarah loves traveling and exploring with her 4-year-old son, Harry. Harry has a personality as big as his smile and loves to share stories of his vacation adventures with friends through pictures and souvenirs. She shows him the world through travels to exciting destinations, often while enjoying luxury hotels and resorts. Sarah and her husband hope to use WellTraveledKids.com to give even more kids opportunities to learn, grow and travel.

7. Live Music Outdoors

As the oldest outdoor music fest in the states, Ravinia Festival is a mainstay of Chicago culture. A series of concerts in Ravinia Park entertain residents and tourists between June and September.

“I would like to catch a concert at Ravinia. Best outdoor music venue around!” – Lauren Monitz

Lauren “Lo” is a travel and food writer from the Windy City currently based in Denver. An adventurer and (mis)adventurer, her goal is to see all 50 states and 50 countries before 50.

8. Electric Riverboat

Electric Riverboat

Renting an electric boat and cruising slowly along the river is a terrific way to unwind. Bring some food and beverages on board for an afternoon of pure relaxation.

“I want to rent one of these electric boats! What a great idea. All of my life I’ve wished I had a boat in this city, but, tour guides you know, we’re not rich! It’s just something a lot of us would never have access to. But now, anyone can rent one of these boats and have the experience only a select few have had.  I love that you can captain them yourself and you can bring food and some beer on board. How fun is that? No going out on the lake on these puppies, but cruising up and down the river for a few hours sounds like the most perfect afternoon ever.”- Margaret Hicks

Margaret Hicks is a comedian, author and owner of Chicago Elevated Tours. She loves Chicago so much, she just can’t stop talking about it.

The one thing I would like to do in Chicago this summer is get on a boat and cruise around the lake! Summer is always the perfect time to enjoy a day/night on a boat with friends and truly take in all that our beautiful city has to offer.” – Ashley Taylor Yannello

Ashley Taylor Yannello is a Chicago Lifestyle Blogger + Stylist + Healer all about Fashion, Beauty, Spirit & Wellness.

9. Manhattans at John Hancock After a Long Day

Bacon Whisky

Chicago has so much to offer that it can be exhausting. Enjoying an outstanding drink at the Signature Lounge in the John Hancock is a great way to end the day, especially when guests make it in time to witness the sunset.

“On my last visit to Chicago I watched the New Zealand All Blacks rugby team play at Soldier Field, ate the ridiculously good caramel and cheese popcorn from Garrets, played tourist with the tourists on a mafia bus tour, ate more than my fair share of deep dish pizza and sailed up the river staring at buildings. But the one thing I would say is a must-do this summer is have a sunset cocktail in the Signature Lounge at the top of the John Hancock building. Tell them you’ll wait for a window seat to drink in the twinkling lights of the end of the day, then make sure you order the sensational Maple Bacon Manhattan ($15), it’s Jim Beam maple with butterscotch and a rasher of smoky bacon. Truly, you’ll thank me later!”  – Megan Singleton

Megan Singleton is the founder of travel blog Blogger at Large. She is based in New Zealand and has been drinking cocktails around the world as a freelance writer for 16 years. Her blog is full of inspiring posts with practical and honest advice and tips to help her readers plan their own travels.

10. Stand-Up Paddle Board

The popularity of the waterfront during summer in Chicago is not a coincidence. One way to enjoy the lakes and river is on a stand-up paddleboard.

“The one thing that is on my list to-do at least once every summer is Stand-Up Paddle boarding! I grew up on the Atlantic, so water is something that I miss all year and make an effort to make up for it in the summer.”- Chrissy Barua

Chrissy lives in Lincoln Park and successfully lawyers by day despite an addiction to bad movies, ice cream and showtunes. She loves to travel both in and out of the kitchen, and spends her free time cooking up exotic dishes from every corner of the globe. You can find her adventures in travel and food on her blog, The Hungary Buddha.

11. Northalsted Market Days

Description – One of Chicago’s many celebrations of culture, Northalsted Market Days features terrific food, bars, nightlife and live entertainment. This event takes place in Boystown, usually over a weekend during the latter half of summer.

“Ever since I first learned about the Northalsted Market Days street fair which takes place in Boystown, I’ve been itching to visit! It’s the Midwest’s largest street fair with food, bars and entertainment all weekend long. Boystown is one of the more fun spots to enjoy Chicago nightlife, so the weekend Northalsted fair must be an even more fun way to enjoy the vibrant, gay-friendly neighborhood! It takes place this year on August 8-9.”- Adam Groffman

Travel blogger Adam Groffman writes about the coolest things to do and see around the world on his internationally popular travel blog, Travels of Adam. You’ll find him most often in Europe, or on Twitter @travelsofadam and Instagram @travelsofadam.

12. Adler Planetarium


Summertime weather makes it more comfortable to set up a telescope and gaze at the sky, but journeying deep into the universe is something best done at the Adler Planetarium in Chicago. This was the first planetarium to exist in the United States, and offers a variety of exhibits and shows that expand and dazzle the mind.

“One thing I’d like to do in Chicago this summer is take my daughter to the Adler Planetarium. She is 6 and genuinely interested in science. She’s been asking to go to the Planetarium since last year and I don’t want to make her wait any longer! She’s also obsessed with Pluto; she doesn’t understand how it once was a planet and now it’s not. Pluto has received some very unfair treatment, as far as she’s concerned. I think she can get answers to her Pluto questions and more with a visit to the Planetarium.”- Francesca Mazurkiewicz

Francesca Mazurkiewicz is a Chicago-based travel blogger at The Working Mom’s Travels and a full-time working mom of two children, ages 6 and 2. Along with her family, Francesca is out to prove that she can have it all – a family, a career, and a travel lifestyle.

13. Kayak and Fireworks

A day trip winding along the Chicago River in appreciation of the skyline architecture, arriving just as the fireworks of Navy Pier begins. At the end, the twinkling light of Chicago at night as you bring the kayak onto shore for a refreshing beverage.

“This summer, I would love to see the Navy Pier fireworks from a different perspective. The best way to leave the crowds behind is to see the shimmering display from the water. Grab a kayak rental or join a tour to paddle down the Chicago River and past the city skyline to Navy Pier, with your arrival coinciding with a spectacular show. While the fireworks are an obvious draw, the entire trip sounds amazing: you start early enough to see towering skyscrapers at sunset and return when the city lights make Chicago magical in its own way. After you’ve worked up a sweat, celebrate your accomplishment by toasting with a Goose Island beer!” – Becky Pokora

Becky Pokora is a travel blogger who thinks Chicago is the USA’s best city! Read about Chicago and other travel adventures at The Girl and Globe.

14. Play the Tourist


Some of the more enjoyable ways to discover Chicago can be to visit the same places that tourists would normally visit. Attending movie nights in Millennium Park, going to museums and other Chicago mainstays never gets old.

“I’d love to carve out time playing tourist in our own city! I enjoy nothing more than grabbing a bag of Garrett’s popcorn (the Chicago mix, of course!) and watching a movie in Millennium Park or taking a stroll through the inspiring museums this city has to offer. A day of shopping on State St and grabbing a cocktail in the Signature Lounge of the Hancock building is always fun, too. Our city has some gorgeous skyline views, and after almost 10 years of living in this town, I never stop smiling when I see those skyscrapers from our back patio.”- Kim Vargo

Kim is one half of the team behind the Chicago based blog, Yellow Brick Home. On any given day, you’ll find her and her husband Scott (her better half, she says) course correcting their way through their 120-year-old house. They’ve taken down walls, turned a kitchen into a bedroom, and love any reason to wear their tool belts for an entire weekend. Alongside their crew of four rescued pets, they’re slowly turning that old house into a dream home.

15. Cloud Gate

Millennium Park features many fantastic events and artistic installations that everyone can enjoy. The Cloud Gate is one of the top attractions as one of the most interesting sculptures in the city.

“We have yet to visit Chicago, and this may be a bit of an obvious answer, but we’d like to see Cloud Gate at Millennium Park. When visiting a city for the first time, we like to see the top tourist attractions first and then delve into the more off the beaten path and quirkier things to do. We always say, ‘There’s a reason things are a top attraction, it’s because they are the best!’ That sculpture looks like a great place to start exploring Chicago.” – Dave and Deb

Dave and Deb are well-known travel personalities in both online and mainstream media. Their highly acclaimed travel blog, The Planet D, won the 2014 Gold Medal for Best Travel Blog by the Society of American Travel Writers. Together they have traveled to more than 100 countries on all 7 continents living by the motto ‘Adventure is for Everyone.’ Follow their weekly travel videos on YouTube and award winning photography posted daily on Instagram.

16. Anthony Bourdain Tour

Celebrities flock to visit Chicago as part of their traveling tours, bringing many different personalities to the Windy City. The “Close to the Bone” tour brings Bourdain into Chicago on July 30th.

“I’d love to go to Anthony Bourdain’s event at the Auditorium Theater on 30th July. I think how he shares his travel and food journey is fantastic!”- Veronica May

From discovering the off-beaten tracks, getting lost in new cities or sipping cocktails on a pristine beach, Veronica always seeking the next adventure. As a world traveler and big time foodie, sharing and inspiring others to experience travel is just as exciting as the journey itself. Find Veronica’s travels over on her blog, Confessions of a Nomad.

17. Chicago Athletic Association Hotel

View from Chicago Athletic Association Hotel

The Chicago Athletic Association Hotel recently finished renovations, reopening their newly completed facilities to the general public after existing as a private club for decades. It now boasts one of the best rooftops in Chicago, with superb views and all-weather access.

“The Chicago Athletic Association, formerly an exclusive private club dating back to the 1890’s, recently underwent a complete makeover and renovation and reopened to the public as the Chicago Athletic Association Hotel.

In addition to the wonderful Venetian Gothic architecture and design, the hotel now boasts one of the best rooftops in the city, with unparalleled views of Millennium and Grant Parks, The Art Institute, and Lake Michigan. I recently dined at Cindy’s, the all-weather rooftop restaurant that also offers an open-air terrace, and I plan to make it a regular stop during my summer outings.”- Christina Solomon

Chritiques is a compilation of my personal and unbiased reviews of restaurants, food products and events. My name is Christina, and I am an attorney, legal business development manager, and lover of all things food, wine, and travel. When I am not navigating Chicago’s restaurant scene, I am running, usually along Chicago’s gorgeous lakefront path, playing golf, spending time with our Cavapoo puppy, Roxie, or traveling to a new city or country!

18. Lobster Truck

The Happy Lobster

Chicago’s incredible food scene would be incomplete without mentioning their fleet of food trucks. The Happy Lobster is reputed to make some of the best lobster rolls in the city.

“Eat at my favorite Lobster Truck– The Happy Lobster. It has the best lobster roll!”- Krista Robertson

19. Architectural Boat Tour

Architectural Boat Tour

Chicago is home to many stunning architectural sites. One of the coolest ways to see all that the Windy City has to offer is to take an architectural boat tour and see all the beauty Chicago has to offer.

I am a huge architecture geek. I planned on being an architect all through high school before I discovered computers so I loved the architecture cruises in Chicago. ”- Chris Christensen

Chris Christensen created Amateur Traveler, a weekly hour-long audio and video podcast, to keep you as far away from tourists wearing jean shorts and Big Johnson T-shirts as possible.

The one thing I truly enjoyed during my trip to Chicago was the Wendella Architectural Boat Tour. The view from the boat was amazing, especially when we crossed into the lake. We took some beautiful photos of the Windy City and its amazing architecture which is an interesting cross between modern skyscrapers and classic buildings. Great way to see the city on a sunny summer day!” – Jessica van Dop DeJesus

Jessica van Dop DeJesus is a Washington, DC is the editor of the food and travel blog The Dining Traveler. She began traveling as a young US Marine 17 years ago and has been to 40 countries on and off duty. All of these experiences gives her broad perspective on food and travel. Her content has been featured in publications such as Travel Channel, USA Today, Budget Travel, Edible DC, Telemundo, and INK361.

“Before the summer comes to an end, I’d love to take the architecture boat tour. I’ve lived in the ‘burbs my whole life, worked in the Loop for 3 years and never taken the tour. My grandfather was a Chicago brick layer, and helped build some of the iconic Chicago structures so I’d love to pay him homage while enjoying a boat ride on the river.” – Chrissy Wojdyla

Chrissy Wojdyla is a Chicago-based writer and humorist. She writes at her personal, no-niche, full-nonsense blog, Quirky Chrissy, where you’ll find her passionately raving about cheese, her hilarious boyfriend, and regularly walking into walls. You can also spot her practicing yoga on Instagram or sharing random and ridiculous thoughts on Facebook and Twitter.

20. A Foodie Tour Around Chicago

Chicago is home to some of the most varied and wonderful food around. Famous for both their gourmet dining options as well as unique local specialties, Chicago is the place to be if you want to sate your stomach.

Chicago in the summertime is as vibrant as can be. As a big foodie and considering that Chicago is one of the premier gastronomy meccas, I’d love to embark on a food tour through the city and try all the local specialties with history and cultural lessons thrown in. On that same note, I’d also love to go behind the scenes some of the best restaurants and speak with the chefs. ”-Nyssa Chopra

Nyssa is a travel journalist who has lived around the world, calling Paris, Los Angeles, Seattle, Reykjavik, New Delhi, London, and Berlin home, and traveled to 50+ other countries. Her travel style fuses the hidden gems of a local destination’s culture with the finer things in life, redefining the idea of experiential luxury travel. In addition to being the Founder of The Cultureur, she has been featured in the Huffington Post, AFAR, Orbitz, and other international publications.

21. Movies in the Park

Movies in the Park

The 15th annual Movies in the Parks series features more than 240 outdoor screenings of current and classic movies in parks across the city. Bring a picnic basket, blanket, and your friends and family and enjoy a movie in the parks.

I’d like to go to the outdoor movies! All across Chicago they have a summer calendar of Movies in the Parks and best of all they are completely FREE. Last time I was in Chicago I went to see the classic women’s baseball movie A League of Their Own with some people I met at my hostel. We took wine, cheese and blankets and had a little picnic- it was such a good evening!”- Victoria Brewood

Victoria is a vlogger and author of the award winning UK travel blog Pommie Travels. In 2008 she packed her Broadcast Journalism degree into a suitcase to travel and work from anywhere. Since then she has visited over 45 countries and encourages others to see the world, even if it means flying solo!

22. Visit Route 66

Route 66

Route 66 is one of the most iconic roads in America, passing through Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona, and California. For those traveling the roads and looking for historic sites, this is a great place to start or end your travels.

We drove from Santa Monica, CA to Chicago along the Route 66 on a long road trip this summer. It was a fabulous drive and Chicago is a great place to either end or start this famous route!”- Jessica and Laurence

Jessica and Laurence are travel bloggers who both share their travels with their readers on their blogs, Independent Travel Cats and Finding the Universe.

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