A Long Weekend Guide to the Windy City
Nothing beats Summertime Chi
Welcome to Summertime Chi, where the city comes alive with sunshine, delicious eats, and endless adventures. Get ready for a long weekend full of fun in the Windy City!
Explore Lettuce restaurants for your next trip, more Things To Do this month and the Lettuce Summer Guide for more ideas on how to live it up under the sun.
Thursday: Start the Weekend Early
Kick the weekend off right with Thursday night Sing-Along Night at Bub City – Chicago. At 9:00 PM, the DJ starts spinning the biggest hits from every genre (not just country) while music videos play across wall-to-wall screens, turning the whole bar into one giant karaoke party. Grab some props, request your favorites, and sing along like it’s already Friday.
Make a reservation for Sing-Along Thursdays at Bub City – Chicago
Friday: Your Official Welcome to Chicago
It’s your first full day in Chicago, and the first thing on your to-do list is to experience the city from great heights. Head over to the iconic Willis Tower and take in breathtaking views of the city. But before you hit the sky deck, make a stop at Sushi-san – Willis Tower. Treat yourself to fresh maki, nigiri, and more.
View the Sushi-san – Willis Tower menu.
If you’re not a fan of heights, no worries! Grab sandwiches and cookies from Beatrix Market – DePaul Loop for a picnic in the park. Take a leisurely stroll through Millennium Park, marvel at the stunning skyline, and snap some Insta-worthy pics at The Bean (Cloud Gate). #BeanThereDoneThat
For more picnic inspo, view our guide to our picnic carryout faves.
Make sure to stroll down the iconic Michigan Avenue for some shopping! And when you’re in need of a quick lunch or pick-me-up post-shopping, stop by Tallboy Taco and pick up some tacos, or check out The Cookie Bar by Summer House and try signature cookies, specialty iced coffee drinks from La Colombe Coffee Roasters, plus fresh-churned soft-serve and thick shakes!
View the menu at Tallboy Taco.
View the menu at The Cookie Bar by Summer House.
Looking for one of the best happy hour deals in the city? Pop into Gus’ Sip & Dip, which was just named #27 on North America’s Best Bars by The World’s 50 Best, from 4:00 PM – 5:00 PM where a rotating cocktail is available for $6, plus tax.
Check out the Gus’ Sip & Dip happy hour here. Gus’ Sip & Dip is first come, first served.
Keep the Happy Hour crawl going with more of our best happy hours in Chicago!
Now that you’ve worked up an appetite, get ready for dinner at Tre Dita, a Tuscan restaurant from famed Chef Evan Funke. Start with Funke’s signature Schiacciata Bianca, a pillowy Tuscan focaccia, and the Insalata di Cicoria, and be sure to try one (or many) of the handmade pastas, perfect for sharing.
Make a reservation at Tre Dita.
For Friday night, head to Three Dots and a Dash and get tropical in the heart of River North. Sip refreshing cocktails that will transport you to a beach paradise. And when the late-night munchies hit, swing by Ramen-san – River North for some Late Night Fried Rice.
Make a reservation at Three Dots and a Dash.
Make a reservation at Ramen-san – River North.
Saturday: Explore the Lakefront, Lincoln Park and Fulton Market
Start your Saturday with a morning bike ride along the picturesque Lakefront Trail. Soak in the scenic beauty as you make your way up to Lincoln Park. It’s brunch time, and you have some fantastic options! Craving tapas? Cafe Ba-Ba-Reeba! is the place for brunch-worthy tapas. Want to indulge in California-inspired dishes? Head to Summer House – Lincoln Park. Looking for fun French twists on brunch? Say oui to Mon Ami Gabi – Lincoln Park! For a nostalgic brunch experience, stop by R.J. Grunts, a Chicago institution where you can enjoy an all-American brunch like no other. If you’re visiting Chicago with kids, R.J. Grunts is located steps away from the Lincoln Park Zoo.
Make a reservation at Cafe Ba-Ba-Reeba!
Make a reservation at Summer House – Lincoln Park.
Make a reservation at Sushi-san – Lincoln Park.
Make a reservation at R.J. Grunts.
For dinner, venture to Aba’s rooftop patio oasis. With a menu full of Mediterranean mezze dishes and picture-perfect backdrops, your taste buds and Instagram feed will thank you. Located in the heart of Chicago’s buzzing Fulton Market District, there are tons of after dinner spots to hit up for a drink. For any winos, grab a nightcap just down the street at The Oakville Grill & Cellar. Pro tip: The Peanut Butter Pie pairs perfectly with a glass of California red.
Make a reservation at Aba.
Make a reservation at The Oakville Grill & Cellar.
Check out more patio dining options in Chicago.
Sunday: Brunch, Lakeside Escape and City Views
Before another busy day exploring the city, you must fuel up with brunch! River North has a ton of delicious options like Bub City for a hearty country brunch, Ema for a Mediterranean-style brunch, Lil’ Ba-Ba-Reeba! for brunch tapas and sangria, or bop over to Lakeshore East for Miru’s traditional Japanese offerings and classics with an Asian twist.
Make a reservation at Bub City – River North
Make a reservation at Ema – River North
Make a reservation at Lil’ Ba-Ba-Reeba!
Make a reservation at Miru
Check out more delicious spots to brunch in Chicago!
Hanging out on the lake? Pure bliss! Rent a boat and set sail on Lake Michigan. Before you get cruising, make a pit stop at Pizzeria Portofino, where you can park and have a scrumptious lunch from the Boat Catering Menu delivered right to your boat. Savor the flavors with the stunning Chicago skyline as your backdrop. To order, place your order for “Pickup” and include your boat’s name under “Special Requests” so they know who to look for.
View Pizzeria Portofino’s Boat Catering Menu.
Order carryout to your boat from Pizzeria Portofino.
After a day of fun on the water, freshen up and head to Miru for the perfect way to end your long weekend – with delicious food and breathtaking sights! Celebrate your last night in Chicago with Japanese-inspired small plates, cocktails and dessert! From the Chocolate Silk Tart perfect for chocolate lovers to Black Sesame Mochi for those who prefer a nutty richness, you will end on a high note. Miru’s terrace offers unobstructed views of the fireworks at Navy Pier every Wednesday and Sunday.
Monday Morning: Fuel Up and Farewell
It’s time to say goodbye to Chicago, but not before one last treat. If you’re staying in Fulton Market, Streeterville or River North, grab a quick weekday breakfast at Beatrix. The pastry counter has an array of tempting pastries, and a Beatrix Coffee Roasters drink, such as the Banana Bread Cold Brew, will give you the caffeine kick you need for your journey back home.
Make a reservation at the Beatrix location nearest you.
Not ready for the weekend to end? Keep the spirits high and the fiesta going with Lil’ Ba-Ba-Reeba!‘s $22 Sangria Pitcher Mondays! Enjoy any sangria pitcher on the menu for just $22 (plus tax, gratuity not included). Order up a Classic Red, or be adventurous and try their rotating Sangria del Día for a fraction of the price.
