Big-shouldered lakefront city of skyscrapers, museums, deep-dish — and the start of Route 66.
Photo: File:Chicago River ferry.jpg: John Picken derivative work: Georgfotoart · CC BY 2.0 · via Wikimedia Commons
Chicago is the Midwest's flagship city: a walkable, transit-rich metropolis on Lake Michigan where world-class architecture, museums, and a legendary food scene cluster within a compact downtown. It invented the modern skyscraper, and the best way to grasp that legacy is from the water on an architecture river cruise.
For a road-tripper it carries a special hook — the 'Begin Route 66' sign stands downtown at Adams and Michigan, across from the Art Institute, making Chicago the eastern start of the Mother Road, which turns 100 on November 11, 2026. Beyond the Loop, a city of distinct neighborhoods — Pilsen, Wicker Park, Chinatown, Hyde Park — rewards anyone who wanders on foot.
Leave the car parked: the 'L' and a flat, beautiful lakefront make downtown easy without one. Best visited late spring through early fall.
Route 66 starts here. Not near here — the begin sign is on Adams Street at Michigan Avenue, two blocks from the lake, and the first two thousand miles of the most famous road in America run from that corner to Santa Monica. Chicago is also where four interstates meet, which is the less romantic half of the same fact: this city is the hinge of the whole middle of the country.
The begin sign stands on Adams Street at Michigan; the return route runs east on Jackson. The old road leaves the city south-west through Cicero and Joliet, shadowing I-55 for most of Illinois with long drivable original stretches.
Sixteen miles along Lake Michigan with the skyline on one side and open water on the other. Northbound at dusk is the version people remember, and it costs you nothing but the time.
The two interstates run together through downtown as the Kennedy north-west and the Dan Ryan south. Reversible express lanes on the Kennedy switch direction with the rush — read the signs before you commit to them.
If Chicago is not your destination, I-80 crosses well south of the city and the Tri-State Tollway (I-294) skirts the west side. Either beats driving through, and on a weekday both beat it by an hour.
The old alignment through Cicero, Joliet, Wilmington and Dwight carries more surviving roadside Americana per mile than anything further west — the Gemini Giant, the Polk-a-Dot, restored gas stations, painted ghost signs. It runs beside I-55 the whole way, so you can rejoin the interstate whenever you have had enough.
TipLeave from the Adams Street sign in the morning and you will be in Pontiac for lunch. Signage is good in Illinois but not perfect — a Route 66 app or map saves a lot of doubling back.
From Hollywood Avenue in the north to 67th Street in the south, with the beaches, the museum campus and the whole skyline strung along it. It is a parkway rather than a highway — no trucks, tight curves, and a 40 mph limit that is enforced.
TipDrive it northbound in the evening for the skyline, southbound in the morning for the light on the water. The S-curve at Oak Street catches people out every year.
Free and open year-round, Millennium Park is home to Cloud Gate ('The Bean'), back on its plaza since a 2024 renovation, and across Michigan Avenue sits the Art Institute — one of the finest collections of Impressionist and Post-Impressionist painting outside Paris.
Insider tipHit the Bean early morning for crowd-free reflection shots; the Route 66 sign is a block south.
Plan a trip to this spot →The city's signature experience — a docent-narrated boat along the Chicago River, the best way to understand its skyscrapers and design history.
Insider tipThe one paid experience worth booking ahead — 90 minutes, boarding from the Riverwalk at the southeast corner of the Michigan Avenue Bridge. Boats run mid-March through late November, not in deep winter.
Plan a trip to this spot →The 103rd-floor Skydeck features 'The Ledge' — all-glass balcony boxes cantilevered outside the building, with views up to four states on a clear day.
Insider tipGo on a clear day; aim for late afternoon to catch day into sunset. 360 Chicago is the north-side alternative.
Plan a trip to this spot →Navy Pier is free to walk and open year-round, and the 18-mile Lakefront Trail runs past it, linking the north-side beaches to the Museum Campus — the Field Museum, Shedd Aquarium, and Adler Planetarium.
Insider tipRent a bike or take the water taxi; the lakefront is free and the best skyline vantage.
Plan a trip to this spot →Wicker Park for vintage and indie music, Pilsen for murals and Mexican food, Chinatown, and Hyde Park — each a different city, plus Lincoln Park's free zoo.
Insider tipPick one or two neighborhoods per day and explore on foot.
Plan a trip to this spot →The 'Begin Route 66' sign stands at Adams Street and Michigan Avenue, across from the Art Institute — the start of roughly 2,450 miles to Santa Monica, California.
Insider tipThe obligatory start-line photo, and a practical place to begin: Adams is one-way westbound, so you roll straight out of the Loop from the sign.
Plan a trip to this spot →A defining American food city, built on three signature dishes plus a deep global-neighborhood scene.
Deep-dish pizza (Lou Malnati's, Giordano's, Pequod's), Italian beef dipped in jus with giardiniera (Al's on Taylor Street, Johnnie's out west in Elmwood Park), and the Chicago-style hot dog 'dragged through the garden' on a poppy-seed bun — never ketchup.
Local tipTry tavern-style (thin, square-cut) too — it's what many locals actually eat.
Pilsen for taquerias and panaderias, Chinatown for dim sum, Devon Avenue for South Asian, and the West Loop's Randolph 'Restaurant Row.'
Local tipEach neighborhood is a different cuisine — go hungry and ride the 'L' between them.
Chicago has a celebrated, Michelin-starred fine-dining scene centered in the West Loop.
Local tipReserve well ahead for the marquee tasting-menu rooms.
Humid continental on Lake Michigan — hot, humid summers (mid-80s) and cold, snowy, windy winters; the lake moderates the shore but drives lake-effect snow. Rain is fairly even with a summer peak. Best late spring through early fall.
Stay central and use the 'L' — downtown is the easy first-timer base.
Most central and walkable to Millennium Park, the Art Institute, the Riverwalk, and the Museum Campus, with excellent 'L' access.
Booking tipBest for first-timers; the Blue Line links O'Hare straight to the Loop.
The Michigan Avenue shopping corridor and the dense dining district just north of the river — lively and central.
Booking tipWalkable to Navy Pier and 360 Chicago.
Stay along an 'L' line for lower rates and a quick train downtown.
Booking tipLook for a hotel with its own lot a few stops out on an 'L' line — you'll pay a fraction of the downtown garage rate.
Do I need a car?
No, not for downtown. Chicago is one of America's most walkable big cities, and the CTA 'L' plus buses cover everything (use a Ventra card). Parking downtown is expensive — keep the car parked and ride the train.
When should I go?
Late spring through early fall. May and June give you long days before the humidity settles in; September and October bring warm afternoons and thinner crowds; July and August are peak festival season if the heat doesn't bother you. Winter is museum weather.
How many days do I need?
Three to four: one for Millennium Park, the Art Institute, and the Route 66 sign; one for the architecture cruise and an observation deck; one for the lakefront and Museum Campus; plus a neighborhood-and-food day.
What's the one experience I shouldn't skip?
The architecture river cruise. Chicago invented the skyscraper, and seeing the skyline narrated from the river is its signature, can't-replicate experience — book ahead.
Where does Route 66 start?
At the 'Begin Route 66' sign on Adams Street at Michigan Avenue, across from the Art Institute. The road was commissioned on November 11, 1926, so its centennial lands during the 2026 driving season and the Illinois stretch will be busy.
Deep-dish or tavern-style?
Deep-dish is the famous bucket-list bite, but many Chicagoans favor tavern-style — thin, crispy, cut into squares. Try both.
Pick your vehicle, line up the stops on the way in and out, and carry the whole route in your pocket.
