Must try
Local speciality
North America / USA
Milwaukee & Chicago
A 7-day heritage journey through Milwaukee & Chicago, USA — hand-planned by Rachana, with where to stay, what to do and where to eat all mapped out.
- Ideal stay
- 7 days
- Best season
- Year-round
- From
- $3,556–$9,891 pp
The place
About this destination
A 7-day heritage journey through Milwaukee & Chicago, USA — hand-planned by Rachana, with where to stay, what to do and where to eat all mapped out.
My experience
This is Rachana's own 7-day itinerary for Milwaukee & Chicago, USA — the version she'd plan for a close friend. Expect a considered day-by-day plan, the stays worth booking, and the small details that make a trip feel effortless. Everything here is personally travelled and curated — no filler.
LuxuryHeritage & CultureCity Break
Through the lens · 6 frames
Photo journal
01
Day by day
The itinerary
Day 01
Milwaukee: Charm on the Lake
- 01Where to Stay
- 021. The Pfister Hotel – Historic luxury with lake views, art gallery, and spa.
- 032. Kimpton Journeyman Hotel – Stylish, centrally located in the Third Ward with a rooftop bar.
- 04Top Things to See & Do
- 05Milwaukee Art Museum – Iconic “wings” design, vast collection of American and European art.
- 06Harley-Davidson Museum – A must even if you’re not a biker; full of American culture.
- 07Lakefront Brewery Tour – Fun and quirky beer tour with riverfront views.
- 08Historic Third Ward – Chic boutiques, galleries, and the Milwaukee Public Market.
- 09Walk the Riverwalk – Art installations and riverside cafes.
- 10Vegetarian-Friendly Dining
- 11Fine Dining & Casual
- 12Odd Duck – Global small plates, plenty of vegetarian options.
- 13Ardent – Inventive tasting menus with prior vegetarian requests.
- 14On the Bus (in Milwaukee Public Market) – Trendy vegan burgers and shakes.
Day 02
Chicago – Architecture, Art & Iconic Eats
- 01Where to Stay
- 021. The Peninsula Chicago – Classic luxury near Michigan Ave, spa, indoor pool.
- 032. Nobu Hotel Chicago – Sleek modern design, rooftop lounge in the West Loop.
Day 03
Explore Downtown & The River
- 01Millennium Park – The Bean (Cloud Gate), Crown Fountain.
- 02Art Institute of Chicago – One of the world’s best (don’t miss the Thorne Miniature Rooms).
- 03Chicago Architecture River Cruise – Must-do experience, especially at sunset.
- 04Walk or rent bikes along the Chicago Riverwalk.
- 05Althea by Matthew Kenney – Upscale vegan with skyline views (on Michigan Ave).
Day 04
Museums & Lake Michigan Sailing
- 01Field Museum – See Sue the T. rex and ancient exhibits.
- 02Shedd Aquarium – One of the best in the U.S.
- 03Afternoon: Sailing on Lake Michigan – Book a private or group sailboat charter from Monroe or DuSable Harbor.
- 04Daisies (Logan Square) – Pasta-forward and veg-friendly.
Day 05
West Loop + Chicago-Style Eats
- 01Explore Fulton Market and Randolph Street – trendy area full of art galleries and restaurants.
- 02Visit Chicago’s French Market – for food stalls and local bites.
- 03Lunch: at Portillo’s & Barnelli’s – Try their famous vegetarian hot dog (ask for veggie chili).
- 04Street art walk in Wicker Park.
- 05Girl & The Goat – Reserve in advance, great vegetarian shared plates.
Day 06
Shopping + Unique Experiences
- 01Magnificent Mile (Michigan Ave) – Flagship stores & upscale shopping.
- 02Oak Street – High-end boutiques (Chanel, Hermès).
- 03State Street – More mainstream stores like Macy’s, Target, Uniqlo.
- 04Do the Tilt at 360 Chicago – Tilted glass over 1000 feet up at John Hancock Center.
- 05Or book The Chopping Block for a hands-on vegetarian cooking class.
- 06EL Ideas – Creative tasting menu, intimate and avant-garde.
Day 07
Lincoln Park & Relaxation
- 01Stroll through Lincoln Park Conservatory and Lincoln Park Zoo (free!).
- 02Visit North Avenue Beach – Watch paddleboarders and enjoy lake views.
- 03Chicago History Museum – Learn about the city’s incredible past.
- 04Summer House Santa Monica – Great veg options, sunny vibe.
- 05Kālis by Chef Danielle Alex (pop-up/seasonal) – If in town, it’s a Michelin-worthy plant-based experience.
- 06Magnificent Mile (North Michigan Ave) – Department stores, luxury brands, Apple Store.
- 07Oak Street (near Rush St) – Boutique luxury designers.
- 08Armitage Avenue (Lincoln Park) – Indie shops and fashion boutiques.
- 09Fulton Market & West Loop – Trendy local shops, design-forward boutiques.
- 10Live Jazz at Green Mill Cocktail Lounge – Historic speakeasy vibe.
- 11Chicago Theatre Tour – Go backstage of the iconic landmark.
- 12Skydeck at Willis Tower with The Ledge – Glass box over 1,300 feet in the air.
- 13Underground Donut Tour – Fun foodie walking tour (veggie-friendly options included).
What to order
Local cuisine
.jpg%2F960px-Seven-course_tasting_menu_at_Monstera_Bistro%252C_Ljubljana_(48702049837).jpg&w=2560&q=75)
Must try
Local speciality
Farm-to-table tasting menus
.jpg&w=2560&q=75)
Must try
Local speciality
Seasonal vegetarian menus
Must try
Local speciality
Craft cocktails
04
Logistics
Getting there & around
01 · Self-drive
A rental car gives you the freedom to set your own pace between stops.
02 · Domestic flights
For longer legs, short internal flights save a full day on the road.
03 · Airport arrival
A private meet-and-greet transfer is arranged from the moment you land.
The numbers
Budget breakdown
Total · per person
$3,556–$9,891 pp
USD
Breakdown
- Accommodation
- $350–$900 / night
- Food & dining
- $63–$198 / day
- Transportation
- $42–$135 / day
- Activities
- $53–$180 / day
Keep exploring
You may also love
USA
Wyoming & Utah National Parks
A 3-day curated journey through Wyoming & Utah National Parks, USA — hand-planned by Rachana, with where to stay, what to do and where to eat all mapped out.
Read guide
USA
HAWAII - Maui & Kauai
A 11-day curated journey through HAWAII - Maui & Kauai, USA — hand-planned by Rachana, with where to stay, what to do and where to eat all mapped out.
Read guide
USA
Usa East Coast
A 8-day island escape through Usa East Coast, USA — hand-planned by Rachana, with where to stay, what to do and where to eat all mapped out.
Read guide