Summertime Chi
I never knew what was so magical about #SummertimeChi until I braved an entire winter in the Windy City, and stayed to see Summer through. The seasons are so distinct in Chicago, that you have to marvel at the beauty of the changes in the leaves on trees, watching mountains of snow melt from sidewalks and backyards that have been shoveled and piled up for weeks, if not months. The constant snowstorms, hopes of a fool’s Spring, then a second winter, a false Spring, a storm of pollen, then finally Summer makes it all worth it.
Summers average around the 80s°, but you will get the occasional breeze to cool you off on a hot day.
Like anywhere else, the warmer months are popular amongst tourists, so airfare and hotels are generally at their highest this time of year.
Here’s your perfect 3-day itinerary to enjoy Chicago in the Summer.
Arriving in Chicago:
To start your trip to Chicago, you can fly in to either O’Hare or Midway airports and take the train into the city. O’Hare (ORD is located north of Chicago’s downtown city center and its anywhere from 45 minutes to an hour’s ride on the Blue line train. If your destination is on another train line, you can transfer in the Loop to the pink, orange, red, and brown line trains. One round trip on the CTA train costs $2.50 and tickets can be purchased at the train terminal before boarding. You can also download the Ventra app on your phone and pay transit fare with your phone instead of purchasing a fare card.
Midway (MDW) airport is located on the southwest side of Chicago and services Southwest Airlines and many regional smaller airlines.
Public transportation is easily accessible and saves so much stress of looking for and paying to park. I highly recommend!
Also, Lyfts, Ubers, taxis, and the Grab app can also be used. I’d really only recommend driving throughout the city if you plan on venturing outside of the city, or if you absolutely need a car.
Day 1:
Breakfast in South Loop
Start your day in South Loop at HoneyBerry Pancakes and Cafe. There are a few locations throughout Illinois and the Midwest, but the State Street location only offers dine-in service on the weekends. There’s patio seating in warmer months. The portions are huge and the food is delicious. If anything, you have to order the Signature Honeyberry Pancakes.
Visit Grant Park
After breakfast, burn off the calories by walking to Grant Park. Grant Park is home to the Buckingham Fountain, the Bean, aka Cloud Gate, Chicago’s Art Institute, as well as Museum Campus.
Buckingham Fountain
If you’ve seen Love Jones, you have Buckingham Fountain on your to-see list. The fountain was dedicated to the city in 1927, and is one of the largest fountains in the world. The fountain spouts water from October - May from 8am - 11pm and has a light show nightly.
The Bean
Cloud Gate, aka The Bean has been in Chicago’s Grant Park since 2006. It’s a 60+ foot stainless steel sculpture mimicking liquid mercury with a 12-foot underpass that visitors are able to walk under. The surface reflects and distorts the city around it so as you walk closer to The Bean it looks like you’re looking in a funhouse mirror. The Bean is clearly a tourist attraction, and there will likely always be a crowd around, so taking pictures will be a task. My tip is to face west to get a good view of The Bean as well as the skyline to see how the skyline is reflected. Early mornings and weekdays are non-peak times
Explore Navy Pier
From Grant Park, you can either take a stroll and walk ~30 minutes to Navy Pier, or you can take a water taxi. Water taxis are such a unique experience, and run several routes along the Chicago River. You can get a one-way pass for $6 or an all-day pass for $10. Once you arrive at Navy Pier, spend the entire afternoon there.
During the summer, Navy Pier has live firework shows starting at 9:30 pm and 10:15 pm. To spend the entire day at Navy Pier, of course take a ride on the ferris wheel to get a bird’s eye view of Chicago as well as Lake Michigan. Besides the ferris wheel, there are other carnival-type rides such as a carousel and a shooting tower. For kids, Chicago’s Children’s Museum is located here at the main entrance and Chicago’s Shakespeare Theatre is housed at Navy Pier. There are many eateries at Navy Pier including quick bite restaurants, chains, and local staples. If you have no other plans to try a Chicago deep dish, you might as well stop in Giordano’s at Navy Pier. An absolute must is to get an Original Rainbow Cone. The ice cream shop has been around for almost a century and serves up 5 slices of flavors (chocolate, strawberry, pistachio, orange sherbet, and Palmer House, which is vanilla ice cream with walnuts and cherries) in cones or cups.
There are shops and pop-ups inside Navy Pier as well as a mini funhouse maze.
Along Lake Michigan, you’ll see dozens of boats, ranging from speed boats, dinner cruises, and sightseeing cruises ranging all sizes and boats where you can do private charters.
Walk down to East End Plaza for unobstructed views of Lake Michigan and public art pieces including the USS Chicago Memorial Anchor.
Michigan Ave.
You can finally leave Navy Pier and walk down Michigan Ave aka Magnificient Mile. Walking along, there are hundreds of retailers, department stores including Saks, Nordstrom, Neiman-Marcus, Bloomingdales, and high-end designers including Burberry, Louis Vuitton plus more. I remember being told by a tour guide that Miracle Mile got its nickname because it would be a miracle for you to walk down the Magnificient Mile without buying anything. The vertical shopping district is pretty unique for a big city of Chicago’s size. Most cities have a mall, but Michigan Ave is Chicago’s premier shopping destination.
If you’re having a sweet tooth by now, head to Garrett’s Popcorn on Michigan Ave and order the Chicago Mix which is cheddar cheese and caramel popcorn. If you’ve never had it before it does sound like an odd combination of salty and sweet, but honestly it is so delicious and addicting. What’s great about Garrett’s is that it stays fresh for like a week in the canister so, it’s the perfect souvenir.
360° Observation Deck at Water Tower
While on Michigan Ave, you need to visit The 360° Observation Deck at Water Tower Place. Take the elevator up to the 94th floor of the John Hancock Building to get panoramic views of the city 1,000 feet off the ground. As the name entails, you see Chicago and more from a 360° view through floor-to-ceiling windows. The Observation Deck also has a tilt ride where a portion of the glass wall extends out from the building and riders feel like they're leaning over the edge of the building. There’s a full bar on-site to give you liquid courage and a souvenir shop to commemorate the moment. By now, you’ll realize that I’m obsessed with Chicago’s skyline and think that everyone should see it from every vantage point possible.
Enjoy the Chicago River and Riverwalk
As the sun sets, head over to City Winery on the Riverwalk for live music and drinks. City Winery is on the Chicago River, serving wine, cocktails, and beer. There’s a walk-up bar where you can take your drinks “to go” to sit and sip right on the river. They serve food at this location, but I would skip it to go anywhere else.
Pizzeria Portofino is also on the Chicago River, serving Italian food, and it feels like you’ve been transported to the Italian Riveria by the decor and menu. They specialize in hand-stretched pizzas and Aperol Spritz, offering a variety of flavors. They tend to book up quickly because it’s a compact restaurant, but the aesthetics are it.
They do offer patio seating for a $10 fee per person, so you can view boats on the river and just enjoy an amazing view. Boaters will definitely wave and say hi! What I find cool is that if you’re riding on a private boat, most restaurants along the Chicago River allow for boat docking. Choose where you want to go first, and reach out to the establishment to ask about their docking fees and reservations.
Day 2
Visit West Loop/Fulton Market Neighborhood to Bar Hop
Start your next day by venturing out to Chicago’s West Loop, home of the McDonald’s International Menu where you can order some food items from around the world.
Head a few blocks over to Federales, an open, lofty-style Mexican restaurant. While you’ll stay for the food and tequila, you’re actually coming to ring the bell. For $10 - $11 you’ll take a tequila shot out of an ice shot glass, then throw it at the bell. I don’t know the tradition behind it, or where the bell came from, but it’s fun AF for some reason.
Fulton Market, formerly a warehouse district is now a gentrified entertainment area with corporate HQs popping up. There are many good restaurants, bars, and venues in Fulton Market. Time Out Market is a food hall with 2 dozen restaurants and bars under one roof, representing over a dozen cuisines along with a rooftop area. If you’re in the mood for a lowkey activity or bar hopping, Emporium is an adult arcade with dozens of games and a huge selection of whiskeys
AuCheval have a reputation of being the best burger in the city. The catch is they don’t take reservations, so it’s first come, first serve, and there is always a line, at least an hour long.
If you still want to try their burgers, head to one of their satellite locations Small Cheval, in the Wicker Park neighborhood. Small Cheval is the stripped down version of AuCheval, and only serves the essentials: burgers, fries, shakes, and beer where you can eat out on their patio and watch the train pass by overhead.
Visit Wicker Park Neighborhood
While you’re on Milwaukee Ave. stroll down to see cool street murals, shop with local and chain retailers, and head over to Semicolon Bookstore to grab a book at this Black-owned bookstore. To reward yourself, head over to Kurimu Ice Cream Shop. They serve unique flavors of soft serve and scooped ice cream in just as unique waffle cone flavors as well as bubble teas and ice cream.
Attend a professional game
There are 6 professional sports teams in Chicago: 2 baseball teams, a basketball team, a hockey team, a football team, as well as soccer. I’ve learned that Mid-Westerners take their sports seriously, though not as seriously as down South. Because all of Chicago’s teams perform relatively well, fans show up, and show out at games. Wrigleyville, a neighborhood up north is home to Wrigley Field, where the Chicago Cubs play. The neighborhood has a ton of bars and restaurants and foot traffic along N. Clark Street. If there’s a baseball game happening, you should attend. I was never a sports girl, let alone a baseball girl, but I attended my first MLB game last year to see The White Sox, and it was so much fun!
Day 3:
Architecture Boat Tour
It’s finally time to really explore Chicago’s waterways. Take an architecture tour on the Chicago River. There are many river and lake boat touring companies throughout the city that run from sunrise through sunset. Wendella is apparently the originator of architecture tours in Chicago, and they offer a variety of tour and cruise options. You can oftentimes find them on Groupon offering discounted rates compared to their website. These tours run anywhere from 45 - 90 minutes and you can choose to visit Lake Michigan, the Chicago River, or both. Chicago has a diverse blend of architectural styles throughout the city, from Gothic, Modern, Art Deco, and more. My tour guide was very informative giving us the history on buildings that I’d been passing for months and had no information on.
What I found to be the most interesting was passing through the Chicago Harbor Lock and understanding how the Chicago River and Lake Michigan are separated. So, if you’re a history or nature buff, I highly encourage you to book the river and lake tour.
Once on the boat tour, and probably after you’ve been along the riverwalk, you’ll see people kayaking along the Chicago River and even paddle boarding in Lake Michigan. I think it’s often overlooked that Chicago has beaches. Sure, not clear water and white sand beaches in the Caribbean or waves like the West Coast, but Chicago has miles of shoreline and beaches along Lake Michigan. Head up north to enjoy Plapen near Oak Street Beach. Playpen is where boaters join together for a big party in the lake. Everyone is swimming from one boat to another, playing music, using floaties and water inflatables. During the summer, boaters are usually out every day, but there are crowds during the weekend.
If you’re looking for a more relaxed vibe at the beach, head down to 31st Street Beach where it’s more locals, more chill, and grown.
Dinner at Maple & Ash
To wrap up a beautiful time in Chicago, you have to go to a celebratory restaurant. Maple & Ash in Gold Coast is one of my favorite restaurants in the city. If you happen to be celebrating a birthday, anniversary, or whatever special occasion, you have to come here to makethe day 100% more special. Everything that I’ve had on their menu is delicious, and the service is top tier. They’re a steak and seafood house, but their brunch is chef’s kiss. At any time of day, you need to order a Pornstar Martini or the Espresso Martini.
