Drinks, Dining, and Things to Do

Drinks

Pollyanna Brewing Company

A local gem with a lively taproom and outdoor patio, Pollyanna serves up creative craft beers and hosts live music—perfect for a laid-back hangout with a pint in hand. ($)

Hughie Mcclafferty's Irish Pub

An Irish pub with a sports bar twist, Hughie’s is great for grabbing a Reuben, sipping a Guinness, and catching the game on the patio or inside its classic pub-style digs. ($)

Pollyanna Social

Just down the street from the brewery, this chic cocktail lounge mixes up tasteful drinks like espresso martinis and kiwi margaritas in a cozy, vintage-inspired atmosphere. ($$)

One Eleven Martini Parlour

This speakeasy-style spot is all about good vibes, silky martinis, and soulful music. Try the Lavender Lemon Drop or the Key Lime martini—they’re as dreamy as they sound. ($$)

Dining

Matt's Barbecue

Texas-style barbecue done right! Brisket, burnt ends, and creamy mac & cheese are the stars here, all served in a no frills, rustic setting. ($)

Capri Xpress Lemont

This family-run Italian spot dishes out hearty pastas, crispy calamari, and Mama’s famous meatballs. It’s BYOB, so feel free to bring your favorite bottle and toast to love! ($)

Corner Stone Tavern

Comfort food meets craft cocktails at this welcoming tavern. From boozy milkshakes to fried bologna sandwiches, it’s a good spot to kick back. ($$)

Wooden Paddle

Wood-fired pizzas, artsy cocktails, and a cute atmosphere make this place a must. It’s perfect for groups—just order a few pies and enjoy! Our favorites are “Smoke & Shrooms” and “Grandma’s Pie.” ($$)

Barrel & Vine

Upscale but relaxed, Barrel & Vine offers New American cuisine with standout dishes like short rib bolognese and portobello steak. Great wine list, great ambiance. ($$$)

Things To Do Nearby

Waterfall Glen Forest Preserve

One of Rachel’s favorite hiking spots at which she spent many sun-soaked afternoons during the covid-era. With over 11 miles of trails and the picturesque Rocky Glen waterfall, it’s a great spot to stretch your legs and soak in some nature. (FREE)

Sagawau Environmental Learning Center and Sagawau Canyon

A peaceful spot for lovers of the natural world such as ourselves. Sagawau offers scenic hiking trails, birdwatching, and educational programs about local geology and wildlife (our typa shit!) The canyon is a hidden gem with trails through rare dolomite prairie. (FREE)

Graue Mill & Museum

Step back in time at Illinois’ only operating waterwheel gristmill for some old-timey vibes. This historic site offers hands-on demos of 19th-century milling, spinning, and weaving, plus exhibits on its role in the Underground Railroad. Fun Fact: Rachel's parents did their wedding photos here! (FREE)

Brookfield Zoo

One of the top zoos in the country, Brookfield spans 235 acres and features over 3,000 animals. From dolphin shows to koalas and a massive carousel, it’s a great day trip for families and animal lovers. ($$)

The Forge Adventure Park & Ziplines

Whether you’re up for a chill round of mini golf ($10/person) or ready to go all out with ziplining, archery, paddlesports, laser tag, and climbing towers, The Forge has something for every energy level across its 300-acre outdoor playground. ($-$$$)

Challenge Accepted Escape Rooms

Put your puzzle skills to the test in these immersive, private escape rooms. Each game is packed with clever clues and dramatic storylines—perfect for groups looking for a fun indoor adventure. ($$)

Things to do in Chicago

Chicago Riverwalk

Stretching 1.25 miles along the south bank of the Chicago River, the Riverwalk is packed with waterfront restaurants, wine gardens, public art, kayak rentals, and boat tours. It’s a scenic spot to stroll, sip, and soak in the skyline. (FREE)

Millennium Park & the Bean

Snap a selfie at Cloud Gate (aka “The Bean”), stroll through Lurie Garden, or catch a free concert at the Jay Pritzker Pavilion in this vibrant urban park. (FREE)

North Avenue Beach

Relax on the sand, rent paddleboards or jet skis, or grab a drink at the beach house—all with stunning views of the skyline and Lake Michigan. (FREE) https://www.chicagoparkdistrict.com/parks-facilities/north-avenue-beach

Shedd Aquarium

Dive into aquatic adventures with beluga whales, penguins, sharks, dolphins, and more at one of the best indoor aquariums in the world. ($$)

Field Museum

Home to SUE the T. rex and Máximo the Titanosaur, this world-class natural history museum offers fascinating exhibits on ancient cultures, evolution, and the natural world. Rachel did a summer internship here and is in love with the place. ($$)

Griffin Museum of Science and Industry

Explore a captured WWII submarine, walk through a mirror maze, and experience hands-on, interactive science exhibits in one of the largest science museums in the Western Hemisphere. ($$)

The Art Institute of Chicago

See masterpieces by Monet, Van Gogh, and Picasso in this world-renowned museum with the largest collection of Impressionist art outside of Paris. ($$)

Museum Of Contemporary Art Chicago

Discover bold, thought-provoking works from today’s leading artists in this sleek museum near the Magnificent Mile. ($)

Skydeck Chicago

Located on the 103rd floor of Willis (Sears) Tower, SkyDeck offers jaw-dropping views of the city and beyond. Step out onto The Ledge—glass boxes that extend 4.3 feet from the building—for a heart-pounding photo op 1,353 feet in the air. ($$)

Chicago River Boat Architecture Tours

Hop aboard for a scenic 90-minute cruise through the heart of the city, where expert guides share the stories behind Chicago’s iconic skyline. ($$)