After settling in, head to Intelligentsia Coffee on Broadway for a smooth cold brew, then wander east to Millennium Park to snap photos with the iconic Cloud Gate sculpture and watch the playful water jets of Crown Fountain. A short stroll brings you to the bustling Chicago Riverwalk, where you can enjoy river-front views and perhaps a quick bite from a waterfront vendor.
After the riverwalk, head to the soaring Willis Tower Skydeck, where floor-to-ceiling glass boxes let you glimpse the cityscape as the sun dips over Lake Michigan. Then wander down to the ornate Chicago Cultural Center, admire its dazzling stained-glass dome, and finish the day with a classic deep-dish dinner at Lou Malnati's on bustling State Street.
As the sun sets, head to The Chicago Theatre on State Street to admire its iconic marquee and catch a live performance or classic film. Afterwards, laugh the night away at Second City Comedy Club, where many famous comedians got their start. Cap the evening with panoramic city views and a handcrafted cocktail at The Signature Lounge atop the John Hancock Center, sipping while the skyline twinkles.
Begin with a guided glimpse inside the majestic Chicago City Hall, then stroll to the historic Rookery Building to marvel at its Frank Lloyd Wright-designed lobby. Continue on to the grand Chicago Union Station, where you can enjoy a coffee beneath its soaring vaulted ceiling, and finish the morning with a photo at the resilient Chicago Water Tower, one of the few structures to survive the Great Fire.
After lunch, wander across the iconic Michigan Avenue Bridge for sweeping views of the Chicago River, then stroll to the gleaming Wrigley Building to admire its white terra-cotta façade and historic clock tower. Cap the afternoon with a peek inside the art-deco marvel of the Merchandise Mart, exploring its grand atrium and sampling a bite at its legendary food court.
After a day of historic sightseeing, unwind with a sumptuous dinner at The Gage, a refined tavern tucked into a historic alley on Upper Michigan Avenue offering modern twists on classic fare. Then glide onto the Chicago Symphony Orchestra stage at Symphony Center for an unforgettable performance beneath its grand chandelier, and finish the night with a craft cocktail at the hidden speakeasy The Violet Hour, where Prohibition-era ambiance meets contemporary mixology.
Start your day with a sunrise stroll along the lakefront before diving into the Field Museum, where you can marvel at the towering Sue T-rex and explore the immersive Hall of Ancient Egypt; then wander across to the Shedd Aquarium to glide through the mesmerizing Amazon Rising exhibit and catch a playful dolphin show, wrapping up the morning with panoramic city views from the historic Adler Planetarium's Stellarscope dome.
After lunch, cross the lakefront to the Art Institute of Chicago, where you can wander through its world-renowned Impressionist galleries and snap a selfie with the towering Modern Wing sculpture. Then stroll down to the nearby Maggie Daley Park, grabbing a craft coffee at The Park Grill while enjoying panoramic views of the skyline and the shimmering lake beyond. Conclude the afternoon with a quick stop at the Chicago History Museum, immersing yourself in interactive exhibits that trace the city's rise from a frontier outpost to a modern metropolis.
After a day of museum-hopping, dine al fresco at Cindy's Rooftop overlooking Lake Michigan, where the menu pairs seasonal Midwestern fare with sweeping skyline vistas. Then wander down to Jazz Showcase on the South Loop for an intimate set of live jazz, and cap the night with a handcrafted cocktail at the speakeasy-style The Violet Hour, letting the city's lights flicker through its plush, Prohibition-era décor.
Start the morning with a leisurely bike ride along the Chicago Lakefront Trail, heading east to the sparkling waters of 31st Street Beach where you can dip your feet and soak up sunrise views over Lake Michigan. Continue to the grand Buckingham Fountain in Grant Park, marveling at its choreographed water shows while sipping coffee at the nearby Harbor House waterfront café. Finish with a brief paddle-boarding session from the Chicago Harbor Lighthouse, letting the gentle lake breezes energize you for the day's adventures.
In the early afternoon, paddle over to Navy Pier, where you can soar above the lake on the iconic Centennial Wheel for panoramic views of the skyline and Lake Michigan, then stroll through the bustling Pier 5 marketplace for a quick bite of fresh seafood and local brews. Afterward, catch a matinee performance at the waterfront Chicago Shakespeare Theater or rent a kayak from Kayak Chicago to explore the lake's gentle waters up close, rounding out an active lakeside experience before the evening.
As twilight settles, board a sunset sail with Chicago Harbor Cruises for panoramic views of the illuminated skyline reflected on Lake Michigan. After disembarking, enjoy a lakeside dinner at Riva Row Kitchen & Bar, savoring fresh seafood while the city lights dance across the water. Conclude the night with a stroll through Maggie Daley Park's illuminated play garden, where the whimsical light installations create a magical finish to your adventure.
After a leisurely breakfast at The Bongo Room on Michigan Avenue, set out for a final shopping spree along the Magnificent Mile, hunting for unique gifts at the designer boutiques of Nordstrom, the tech-savvy Apple Store, and the iconic Water Tower Place mall. Then, squeeze in a quick interactive visit to the Chicago Architecture Center for a hands-on exhibit on the city's skyline before catching your ride to the airport, souvenirs in tow.
After lunch, wander east to Eataly Chicago in the River North district for a gourmet sampling of fresh pasta and Italian pastries, then take a short walk to Oak Street Beach where you can stretch your legs on the sandy shoreline and snap a final photo of the lake skyline. Finish the afternoon with a soothing treatment at the Peninsula Spa in the Peninsula Chicago, recharging before your journey to the airport.
For your final night, indulge in a farm-to-table dinner at The Publican in the West Loop, where the wood-grilled meats and house-made charcuterie perfectly capture Chicago's Midwestern spirit. Afterwards, sip a farewell cocktail at The Berkshire Room, a sleek speakeasy known for its inventive drinks and intimate ambiance, before heading to the airport with memories of the city's vibrant flavors.
| Place / Activity | Cost |
|---|---|
| Intelligentsia Coffee | $5 |
| Millennium Park | Free |
| Chicago Riverwalk | Free |
| Willis Tower Skydeck | $35 |
| Chicago Cultural Center | Free |
| Lou Malnati's | $30 |
| The Chicago Theatre | $30 |
| Second City Comedy Club | $25 |
| Signature Lounge | $15 |
| Rookery Building | Free |
| Chicago Union Station | Free |
| The Gage | $40 |
| Chicago Symphony Orchestra | $50 |
| The Violet Hour | $15 |
| Field Museum | $32 |
| Shedd Aquarium | $39 |
| Adler Planetarium | $22 |
| Art Institute of Chicago | $25 |
| Maggie Daley Park | Free |
| The Park Grill | $20 |
| Chicago History Museum | $15 |
| Cindy's Rooftop | $45 |
| Jazz Showcase | $20 |
| Chicago Lakefront Trail | Free |
| Harbor House | $15 |
| Centennial Wheel | $15 |
| Chicago Shakespeare Theater | $35 |
| Kayak Chicago | $30 |
| Chicago Harbor Cruises | $40 |
| Riva Row Kitchen & Bar | $35 |
| The Bongo Room | $20 |
| Chicago Architecture Center | $12 |
| Eataly Chicago | $30 |
| Peninsula Spa | $150 |
| The Publican | $45 |
| The Berkshire Room | $15 |
| Estimated Total (per person) | $890 |