Chicago is a big city no doubt, but take it step by step and you can cover a lot of ground in a single day. With a short list of restaurants, and a lot of sightseeing along the way, this Chicago guide will take you through the major downtown highlights. Take heed: good walking shoes are clutch for this itinerary. Pants with an expandable waistline aren’t a bad idea either.
Chicago’s walk score always rises up to the top in the annual rankings of the nation’s best walkable cities, with the downtown city center practically acing the test. It won’t take long to get your bearings with the easy-to-navigate grid. The city is neatly aligned into square blocks with most streets running north/south or east/west. Main things to keep in mind: Lake Michigan serves as the anchor to the east and the Chicago River creates a natural border, separating the Loop from The Magnificent Mile and West Loop.
The perfect one-day walking tour of Chicago
This itinerary dials in on the downtown core. Of course, your map app is probably doing all the heavy lifting here in terms of directions, so here’s the lowdown on the good stuff:
The Magnificent Mile
Start on North Michigan Avenue at the Historic Water Tower, a surviving relic of the Great Chicago Fire and a symbol of the city’s spirit during the time of renewal afterward. It has been adapted for a different use now (an art gallery), while the Pumping Station across the street still pumps water for the city.
Gear up for a busy morning with a solid breakfast. For the early riser here are two nearby options: NoMI Kitchen, a more posh setting with a pretty view, and Wildberry, a local brunch chain with a whopping 100+ menu items to choose from.
Either way, you are only steps from 360 CHICAGO, where soaring views from 1,000 feet above await.
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Elevators jet up to the 94th floor at a rapid pace, and once you step off, you’re immediately hit by the bright blue hues of the sky and lake. Floor-to-ceiling windows on all sides offer 360-degree views, but it’s the side with the moving glass thrill ride Tilt that you can’t miss.
Back on the ground, 460 stores beckon. Reason number one that people come to The Magnificent Mile is for the shopping. Browse a bit at this northern end of the 13-block district, where high fashion boutiques like Gucci and Louis Vuitton are intermixed with style-savvy brands like Uniqlo and Topshop.
Garrett Popcorn Shops on the seventh floor of Water Tower Place is just enough out of the way to not have the crazy long lines of the other area locations. Stop here for the classic Chicago snack, a bag of Garrett Mix — the world famous cheddar and caramel popcorn combo.
On to Oak Street Beach, just a few blocks north continuing on Michigan Avenue. Sandy shores and palm trees line the waterfront. Dip your toes in the lake and sink into the soft sand.
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Looking back downtown, you see the skyline from a different direction, now looking south. This is the way you’re headed next because the Lakefront Trail will take you right to Navy Pier. The popular promenade is one mile away and every bit of the way is scenic.
If you haven’t had enough of the views, ride the Centennial Wheel.
Otherwise, the vintage carousel and colorful wave swinger in Pier Park is a throwback to simpler times. Assuming you’re here just for the walk through — as opposed to visiting the Chicago Children’s Museum or Chicago Shakespeare Theater, or catching the evening fireworks or an IMAX movie — enjoy the breezy stroll and be on your way. A late lunch is on the schedule.
This is a town full of famous, award-winning chefs. Go the quick-casual route with Mexican street food from TV host, author and celebrity chef Rick Bayless at XOCO.
Or for another counter service option, cross off bucket list eats like the Italian beef and Chicago-style hot dog at Portillo’s.
Walk a few blocks south and cross the Chicago River. The newest outdoor gathering place is the south bank of the waterway, just steps below the street level. The Chicago Riverwalk is lined with restaurants and bars — it practically runs on rosé in the summer.
While you watch the boats go by, look up and admire the architecture. You would need a whole guidebook to list all the great buildings. But for starters, there’s the Wrigley Building and its majestic clock tower, the Gothic Revival Tribune Tower and Beaux Arts London Guarantee Building anchoring the Michigan Avenue intersection.
Make your way up the stairs to upper Wacker Drive at State Street. Only a block from the Chicago Riverwalk is a Loop landmark built in 1921. The Chicago Theatre was an opulent movie palace, one of the earliest and largest constructed in America. Snap a photo of the famous marquee and note the encircled “Y” insignia that radiates from the center “C” in C-H-I-C-A-G-O. It represents the fork where the Chicago River splits into three branches.
Turn to walk east on Randolph Street. You’re headed to Millennium Park, the biggest attraction in the Midwest.
It’s home to a giant stainless steel sculpture that charms everyone, a playful piece of public art. Cloud Gate is known more by its casual nickname, “The Bean”. Pictures here are a must. Another whimsical piece is Crown Fountain, a set of glass block towers that bookend a reflecting pool.
Depending on your time, you can visit more areas of Millennium Park Campus, like the Chicago Cultural Center (explore the free art galleries and see the world’s largest stained glass Tiffany dome) or Maggie Daley Park (where you can tackle the climbing wall).
Otherwise, push on into other areas of the surrounding lakefront park to find Buckingham Fountain.
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It’s one of the largest in the world and its powerful jets create a beautiful water display every hour.
Head out of the park and into the Loop proper — this is the area bounded by the ‘L’ train tracks, which form a rectangular loop. It’s studded with historic skyscrapers and landmark buildings. Depending on what strikes you (and what buildings are open since the hours vary), that could include the stately Monadnock Building, the light-filled Rookery, the Mid-Century Modern Federal Center, or the 19th-century Marquette Building.
For one final public art piece in the Loop, make a stop at Daley Plaza and study The Picasso. Your interpretation of this 50-foot tall steel sculpture is as good as any, since artist Pablo Picasso never did offer an explanation of what it represents when he gifted it to the city in 1967.
The West Loop sits just west of the Loop — no surprise there. Walk down Randolph Street and cross the Chicago River again, this time at the South Branch. The last downtown neighborhood you’re exploring is a story of contrast and change. What was once filled with wholesale markets and commercial storage buildings shifted to restaurants, residences, and modern office buildings.
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End of day. Finish with dinner and dessert, then put your feet up. The area known as “Restaurant Row” has swelled and extends beyond Randolph Street, now a full blown dining and nightlife district that encompasses Fulton Street, Lake Street, Washington Boulevard and Madison Street.
Try crowd favorites like Bar Siena paired with BomboBar treats from the adjoining takeout window or Federales followed with a stop at neighboring Do-Rite Donuts & Chicken. Or find more hearty fare — well deserved after walking nearly 10 miles through downtown Chicago — at acclaimed West Loop eateries that are Bib Gourmand picks like The Publican, Au Cheval, and BellyQ.
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