After your 8:51 AM arrival at ORD, drop bags near the hotel and warm up with a hearty brunch at Wildberry Pancakes & Café, just a short walk from Millennium Park-expect signature pancakes and quick service ideal for a winter morning. Then stroll through the crisp air to admire Cloud Gate (The Bean) for iconic photos, followed by a cozy, hands-on exploration of local stories at the Chicago History Museum, which offers indoor exhibits to escape the cold and learn about the city's past before check-in.
After check-in, warm up with a cozy late-afternoon coffee and pastries at Dollop Coffee Co. before heading out to explore the nearby indoor galleries at The Art Institute of Chicago for masterpieces and a relaxed stroll through heated halls. Finish the afternoon with a scenic, covered river cruise from Chicago's Riverwalk (many operators run heated indoor boats) to see the city's architecture as the lights come on, setting you up for dinner near the hotel.
After freshening up, take a short walk to enjoy riverfront views and craft cocktails at Cindy's Rooftop, where heated seating and skyline vistas make for a warm, memorable sunset. For dinner, head to Joe's Seafood, Prime Steak & Stone Crab for an upscale meal-reserve a table riverside if possible-then finish the night with live jazz and late-night drinks at the intimate Andy's Jazz Club & Restaurant to soak in classic Chicago nightlife before turning in.
Start your morning with a comforting breakfast at Beatrix near the Magnificent Mile for seasonal bowls and strong coffee, then stroll to the nearby Museum of Illusions for playful mind-bending exhibits that pair perfectly with the colorful energy you're headed to later. Afterward, warm up indoors at The Chicago Athletic Association's Cherry Circle Room for a classic cocktail or hot toddy before making your way west to the immersive installations at the Wonder Museum.
Wander over to The Rookery Building for a guided architecture tour and to admire Frank Lloyd Wright's landmark lobby, then duck into nearby Terzo Piano at the Modern Wing for a light lunch with museum-quality views. Afterward, warm up with coffee and pastries at La Colombe before exploring the indoor galleries and rotating installations at the Museum of Contemporary Art Chicago-perfect prep for an evening of pizza and game-day energy.
After the museum and a city wander, head to The Purple Pig for shared Mediterranean small plates and a lively atmosphere that pairs well with pre-game conversation, then walk over to Bangers & Lace for craft beers and gourmet sausages while the pre-game buzz builds on the TVs. Finish the night at The Aviary, where inventive cocktails and theatrical presentations make for a memorable late-evening celebration before returning to your hotel.
Enjoy a relaxed final morning with breakfast at The Original Pancake House for classic, hearty favorites before a short, calming stroll to browse design-forward goods at Water Tower Place and warm up with a specialty pour at Dollop Coffee Co.. If time allows, squeeze in a focused visit to the nearby Museum of Contemporary Art Chicago for one last dose of art in heated galleries before heading back to the hotel to collect bags and depart for ORD.
After checkout, pop into Eataly Chicago for a leisurely Italian lunch and grab cured meats or a focaccia to enjoy later; the bustling indoor market is warm, lively, and minutes from your hotel. Then take a short taxi to 360 CHICAGO for skyline views from the heated indoor observation deck and a final photo op before heading to O'Hare-plan to leave the Magnificent Mile by 2:30 PM to allow time for traffic and airport security.
Wind down your weekend with a relaxed pre-flight evening at Caffè Lello, where Italian small plates and aperitifs keep things light and cozy near the hotel, then take a short stroll to The Signature Room at the 95th for skyline nightcaps and panoramic views that feel like a proper farewell to the city. If you prefer something more low-key before heading to the airport, grab a craft sandwich and local pastry to-go from Crosstown Doughnuts & Coffee and enjoy them in the heated comfort of your hotel lobby while finalizing bags and ride arrangements to ORD.