A northbound journey from Hyde Park to Glenview (with lakefront, music, and North Shore add‑ons)

• Chicago is safe-ish, but use big-city common sense: do not leave anything visible in your car. Always put bags and luggage in the trunk.
• Most hotels won’t be ready until 3:00 pm. So if you are arriving early on Friday and you’re staying closer to the airport or suburbs, it’s usually best to head straight into the city and start sightseeing rather than waiting around.
• Chicago has toll roads. If you’re renting a car, set up Pay By Plate for the dates you’re driving: https://agency.illinoistollway.com/paybyplate
• Parking note: Chicago is brutal about parking enforcement. Almost all street parking requires payment.
  • Download the ParkChicago app and pay attention to posted signs.
  • Downtown tip: The easiest way to park is using SpotHero. There are many garages that are far cheaper than street parking and much less stressful.
  • Time limits, street sweeping, and tow zones are strictly enforced.
  • When in doubt, garages are safer than street parking.

Chicago sits on Lake Michigan, one of the largest freshwater lakes in the world. On windy days it genuinely looks and feels like an ocean—waves, wide horizon, sandy beaches, and big skies.

• Lake Shore Drive – The iconic road hugging the lake. Great for a scenic drive with skyline views on one side and open water on the other.
• Chicago Lakefront Trail – An ~18‑mile paved path running along the water. Perfect for walking, biking, or just stretching your legs while taking in views of the city and lake.

Lake Michigan faces east, so sunrises are absolutely possible if you’re up early.

• Friday 3/13: Sunrise ~6:20 am | Sunset ~6:01 pm
• Saturday 3/14: Sunrise ~6:18 am | Sunset ~6:03 pm
• Sunday 3/15: Sunrise ~6:16 am | Sunset ~6:05 pm

• Ohio Street Beach – Easiest downtown beach access, great skyline views, right near Navy Pier.
• Oak Street Beach – A bit north, classic Chicago beach feel.
• North Avenue Beach – Lively, iconic, and very walkable from Lincoln Park.

If you’re staying farther north (including Sheraton Northbrook), these are often easier and less crowded:

• Rogers Beach (Rogers Park) – Quiet, neighborhood beach with a wide shoreline.
• Loyola Beach (Rogers Park) – Peaceful, scenic, and great for a short walk by the water.
• Hartigan Beach (Rogers Park) – Smaller and very local-feeling.

These beaches connect directly to the Lakefront Trail and are great for a calm lake walk without downtown crowds.

• Ohio Street Beach – Easiest downtown beach access, great skyline views, right near Navy Pier.
• Oak Street Beach – A bit north, classic Chicago beach feel.
• North Avenue Beach – Lively, iconic, and very walkable from Lincoln Park.

A classic Chicago stop and an easy way to get lake and skyline views all in one place.

• Walk the pier, ride the Centennial Wheel, grab snacks, and enjoy views back toward the city.
• Fireworks: Navy Pier fireworks are a summer tradition only. There are no scheduled fireworks in mid‑March.

Vibe: Historic, academic, lakefront

The furthest south neighborhood most visitors go to. Home to the University of Chicago, whose Gothic buildings make it feel like Hogwarts.

• University of Chicago Campus – Walk the quads and admire the architecture.
• Museum of Science and Industry – One of the largest science museums in the world.
• Frank Lloyd Wright Home (Hyde Park) – Lesser-known FLW site in the neighborhood.
• Promontory Point – Lakefront views back toward the skyline.

Food

• Virtue – Upscale soul food.
• Valois – Cafeteria-style counter. Cash only.

Music History Stop

• Muddy Waters’ Home
  4339 S Lake Park Ave, Chicago
  Exterior only. Home of the legendary blues musician who helped define the Chicago blues sound.

Vibe: Cultural history, museums, architecture

All three are clustered together along the lake:

• Shedd Aquarium – One of the largest indoor aquariums in the world.
• Adler Planetarium – Space science with incredible skyline views.
• Field Museum – World-class natural history museum (home of Sue the T‑Rex).
• Chess Records / Willie Dixon’s Blues Heaven Foundation (2120 S. Michigan Ave)
  • Legendary studio where Muddy Waters, Howlin’ Wolf, and Chuck Berry recorded.
• Clarke House Museum – Oldest surviving house in Chicago (built 1836).

Vibe: Food‑focused, lively, walkable

Great place to park once, walk around, browse shops, and eat.

• QXY Dumplings – Handmade dumplings; extremely popular.
• Walk along Wentworth Avenue for bakeries, bubble tea, and casual spots.

Vibe: Classic Chicago, architecture, iconic sights

• Willis Tower – Skydeck & Glass Ledge – Step out onto the glass floor 103 stories above the city.
• Chicago Architecture Center River Cruise – One of the best ways to understand the city.
• Millennium Park – Cloud Gate (The Bean), Crown Fountain, gardens.
• Art Institute of Chicago – World-class museum.
• Museum of Contemporary Art (MCA) – Modern and contemporary art (220 E Chicago Ave).
• Chicago Public Library – Harold Washington Library Center – Massive, beautiful library and an easy architectural walk-through.

Iconic Streets & Sights

• Chicago Theatre & Marquee Sign (State Street) – One of the most recognizable signs in the city and a classic photo stop. The theater hosts concerts, comedy, and touring shows.
  • Full show calendar: https://www.msg.com/calendar/chicago-theatre
• Michigan Avenue (The Magnificent Mile) – Flagship shopping, historic buildings, and classic city energy.
• Wrigley Building & Tribune Tower – Landmark riverfront architecture.

River & Food Walks

• Chicago Riverwalk – A fantastic place to stroll, sit by the water, and see the city’s architecture from below.
• French Market – Casual food hall with lots of options, great for a quick bite near the river.

Retail & Landmarks

• Starbucks Reserve Roastery – Massive, multi-level flagship Starbucks experience.
• Merchandise Mart – Enormous historic building along the river; once the largest building in the world and still a major design and tech hub.

Vibe: Dining, nightlife, classic Chicago

Deep Dish (Best of the Best)

• Lou Malnati’s – Classic buttery crust Chicago deep dish.

Restaurants

• Bavette’s – Dark, old-school Chicago steakhouse.
• The London Chop House – Historic steakhouse with live jazz and a Rat Pack-era feel.
• Au Cheval – Famous burger.
• Trivoli Tavern – Cozy Italian-leaning tavern.
• Avec – Mediterranean / Middle Eastern small plates.
• Momotaro – High-end Japanese sushi.
• Kasama – Famous Filipino brunch; also has a Michelin star.

Rooftops & Views

• Cindy’s Rooftop – Overlooks Millennium Park and the lake.
• LondonHouse Rooftop – Excellent river and skyline views.
• ROOF on theWit – Lively rooftop scene with city views.

Vibe: Modern food scene, high energy

• Pequod’s Pizza – Deep dish icon with caramelized crust; many locals say it’s the best.
• Fulton Market District – Excellent walking and people‑watching.

Food Highlights

• Akahoshi Ramen
• Maxwell’s Trading
• Crying Tiger

Vibe: Green space, family‑friendly

• Lincoln Park Zoo – Free and walkable.
• Lincoln Park Conservatory – Warm and beautiful year‑round.

Vibe: Music, sports, neighborhood feel

• Wrigley Field – Even non‑fans enjoy the surrounding area.
• Metro – Legendary live music venue hosting rock, indie, and touring acts.
• Giordano’s – Stuffed‑style Chicago deep dish.

Vibe: Jazz history, grit, character

• The Green Mill
  • Historic jazz club and former Al Capone hangout.
  • Live music nightly; poetry slam Sundays.
  • Hosted Billie Holiday; Frank Sinatra was a regular.
  • Cash only.

Vibe: Cozy, walkable, great shopping

One of the best neighborhoods in Chicago for strolling, shopping, and eating. This is also a personally meaningful neighborhood for our family.

• Chicago Waldorf School (Laszlo’s school)
  5200 N Ashland Ave, Chicago
  
  • The largest Waldorf school in the nation
  • Built 1908–1909
  • Designed by Dwight H. Perkins, who trained under Frank Lloyd Wright
  • The first Prairie School public school and the first public works building in the Midwest Prairie style
  • An architectural gem from the exterior (not open to the public)
  • Inside is a massive historic auditorium—something to imagine rather than see

Shops & Gifts

• Four Sided – Excellent unique gifts, books, art, and Chicago‑themed items.

Antiques & Vintage

• Woolly Mammoth Antique Mall
• Andersonville Antiques
• Brown Elephant
• Vintage Underground

Food & Stops

• Hopleaf – Belgian beer hall with excellent food.
• Women & Children First Bookstore
• Swedish American Museum

Vibe: Lakefront, residential, low‑key

• Edgewater Antique Mall – Multiple antique vendors.
• Lakefront Trail access – Quieter stretch of the lake.

Vibe: College town, lakefront, great food

• Northwestern University Campus – Beautiful lakeside walks.

Restaurants

• The Barn Steakhouse
• Soul & Smoke
• Oceanique (upscale seafood)

Vibe: Quiet, beautiful, North Shore charm

• Baha’i House of Worship – Stunning architecture and peaceful grounds.
• Plaza del Lago – Historic open-air shopping center.

Dining

• Torino Ramen – Excellent ramen destination. (1024 Wilmette Ave, Wilmette)

Vibe: Calm, family-friendly

• The Grove – Nature preserve with historic buildings.
• Downtown Glenview – Easy walking and dining.

Nearby highlights:

• Asador Bastian – Often cited as one of the best steakhouses in the U.S.
• Home Alone House – 671 Lincoln Ave, Winnetka (exterior only).
• Married with Children House – 641 Castlewood Ln, Deerfield (exterior only).

Chicago has a deep music scene beyond jazz and blues.

Venues to Know

• Metro – Legendary rock and indie venue.
• The Shed / Experimental spaces – Underground and experimental acts.
• House of Blues – Touring national acts.

Vibe: Architectural, historic, walkable suburb just west of the city

Oak Park has the largest concentration of Frank Lloyd Wright homes in the world.

• Frank Lloyd Wright Home & Studio – Core historic site.
• Self-guided walking routes through residential streets.

Complete FLW Oak Park guide and map: https://flwright.org/visit/oak-park

Chicago has a deep, living street art and graffiti culture. Much of the best work exists outside formal galleries—on viaducts, underpasses, industrial corridors, freight lines, and side streets—and it is constantly changing. Think of this less as a museum and more as a moving outdoor archive.

A lot of the strongest work appears in places where infrastructure meets neighborhoods: rail bridges, expressway walls, and service alleys. Walking slowly and staying curious is part of the experience.

• “You Are Beautiful” – One of the most recognizable pieces of street art associated with Chicago. Created by Matthew Hoffman, the phrase has appeared in many locations over the years, especially around the West Loop and Fulton Market. Locations move over time, which is part of its meaning and charm.

These areas consistently feature strong work, even though individual pieces rotate.

• Greenwood Avenue (Lakeview / Uptown border)
  • Known locally for rotating graffiti and murals along walls, garages, and alleyways.
  • Best explored on foot.
• Wabash Arts Corridor (South Loop)
  • Roughly along S. Wabash Ave between Roosevelt Rd and Cermak Rd.
  • A city-supported mural corridor with large-scale, high-quality works on building facades.
• Pilsen – 18th Street Corridor
  • Between Ashland Ave and Halsted St.
  • One of Chicago’s most famous mural neighborhoods, rich in cultural, political, and community-driven art.
• Milwaukee Avenue Corridor (Logan Square / Wicker Park)
  • Look near underpasses, rail viaducts, and side streets off Milwaukee Ave.
  • One of the most active areas for evolving graffiti and street art.
• Lower Wacker Drive & Nearby Underpasses
  • Industrial, cinematic, and layered with decades of graffiti.
  • Frequently recognizable from films and TV shows.
• Lake Street Viaducts (Near West Loop / Fulton Market)
  • Rail bridges and underpasses along Lake St often feature large-scale graffiti pieces.

• Graffiti changes frequently—what’s there today may be gone tomorrow.
• Daytime is best for visibility and photography.
• Stay aware of surroundings and traffic, especially near underpasses.
• Pair graffiti walks with nearby food stops (Pilsen tacos, Logan Square coffee, West Loop dining).

• Valois (Hyde Park)
• The Green Mill (Uptown)

Tip: Chicago is a city of neighborhoods. You don’t need to see everything—pick a few areas, walk, eat, and let the city reveal itself.