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A fresh take on a spring weekend in Chicago
Three days of river walks, lakeside spaces and standout architecture
Chicago's layout is easy to read when you're in it. The streets are structured and everything builds naturally from the river out to the lake. Add in wide sidewalks, open parks and lots of places to stop along the way, and it becomes well‑suited to a long weekend escape.
If you’re passing through or visiting for a weekend in Chicago, move through the city in a way that feels balanced, mixing landmark views, time outdoors and neighbourhood stops without overdoing it.
Friday afternoon: walk the Chicago Riverwalk
Head straight to the Riverwalk to get your bearings. Start around Michigan Avenue and walk west, where you’ll pass some of the city’s most striking architecture up close, including the Wrigley Building and the river bridges that define Chicago’s skyline.
Friday night: rooftop views, then dinner nearby
As the light shifts, head up to a rooftop in the Loop district for your first skyline view. From here, you’ll see the river, Millennium Park and the grid of the city all at once.
For dinner, move slightly west into the West Loop and its "Restaurant Row". Randolph Street gives you options ranging from iconic Chicago-style deep-dish pizza, hot dogs and Italian beef to more upscale, Michelin-starred tasting menus.
Saturday morning: see the city from the river
Food, culture and prohibition-era architecture
Discover Chicago through its iconic sights and signature flavours on a guided walking tour through the city centre. Book this Destination Deal in advance to secure your spot on The Total Chicago Experience.
You'll pass architectural landmarks, explore the hidden Pedway tunnels, stroll along the Chicago Riverwalk and visit Millennium Park's famous Bean sculpture before sampling some of the city's most beloved dishes, including Chicago-style popcorn, a classic hot dog, deep-dish pizza and an authentic beef sandwich.
Take an architectural boat tour
Or trade land for water with an architectural boat tour, one of the most efficient and engaging ways to understand how the city fits together. Chicago’s architecture is perhaps best understood from the water, where its skyline reveals the city's story.
Along the banks, you'll pass everything from historic skyscrapers to newer glass towers, each representing a different chapter in Chicago’s architectural evolution.
Saturday afternoon: head to the lake
Follow the Lakefront Trail
Move east until you hit Lake Michigan. From here, the Lakefront Trail opens up into wide walking routes and cycling paths with uninterrupted views of both water and skyline.
Explore Lincoln Park and Old Town
From the lake, head toward Lincoln Park. Stroll past elegant late-19th-century row houses in the Old Town Triangle or visit the nearby Chicago History Museum. Then, round the afternoon off at St. Michael's Church, one of the few structures to survive the Great Chicago Fire of 1871.
Saturday night: River North after dark
As night falls, spend the last evening of your weekend in Chicago at River North, which lights up with restaurants, cocktail bars and clubs. Expect a strong mix of rooftop bars, speakeasies and high-energy venues all within a few blocks.
Sunday morning: coffee and one last walk
Start with coffee and something simple, then take a final walk, either along the Riverwalk again or through a nearby stretch of downtown. The city shifts depending on the time of day and seeing it once more before the end of your city break in Chicago is more than worth it.
If you find yourself enjoying a Priority Pass experience on your way back, including access to Air France Lounge, be sure to take a quiet moment to reflect on your time in The Windy City.