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Canyon Travels @ USA and Worldwide - 52 Destinations and 19 Countries

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DAY TOURS FROM CHICAGO

Chicago City Tour, Milwaukee & Mackinac Island Trips

See Chicago’s skyline and neighborhoods with a local guide, then venture further to Milwaukee, Galena and Dubuque, Lake Geneva, or car-free Mackinac Island.

  • 🏙️ Chicago city tour
  • 🍺 Milwaukee
  • 🏝️ Mackinac Island
  • 🚐 Downtown pickup
See tours & book ↓ Plan a private day

Barbil Tours runs small-group and private tours from Chicago with complimentary pickup and drop-off from the downtown area. Choose an all-inclusive city tour, a day trip across the Wisconsin or Illinois border, or a longer journey to Mackinac Island.

⭐ Why travel with Canyon Travels
🚐 Pickup & drop-off
We collect you in Chicago and bring you back at the end of the tour. No rental car or route planning needed.
🏡 Local, family-run team
Friendly guides who know the sights, the stories and the best stops.
👥 Small group or private
Share the day with a small group, or book a private tour for just your party.
🗺️ Custom experiences
Tell us your interests and pace, and we'll tailor the day to you.
🏙️ What You Can See
Chicago highlights
The lakefront, famous architecture, parks and neighborhoods with a local guide.
Milwaukee
Wisconsin’s lakeside city, known for its brewing history and landmarks.
Galena & Dubuque
A preserved 19th-century town and a Mississippi River city on the Iowa border.
Mackinac Island
A car-free island in Lake Huron, known for horse-drawn carriages and Fort Mackinac.
🗓️ Best time to go
🌸 Spring
Parks turn green and the lakefront comes back to life.
☀️ Summer (Jun–Aug)
The best time for Mackinac Island and lakeside towns, with long days.
🍂 Autumn (Sep–Oct)
Fall colors along the way to Galena and Lake Geneva.
❄️ Winter
Cold and windy. City tours run, but some island services are seasonal.
ℹ️ Good to know
🏝️ Mackinac Island
Mackinac trips are long days that include a ferry crossing; dress for lake weather.

Tours from Chicago

Private or small group — your choice

Private Private tours from Chicago Just your party, a dedicated guide and a vehicle to yourselves. Go at your own pace and change the plan as you like in Chicago. 2 tours 10 hrs – 16 hrs 30 min from $1,200 See these tours ↓ Small group Small-group tours from Chicago Share the day with a few other travelers. A great value way to see the highlights with a local guide. 4 tours 6 hrs 30 min – 16 hrs 30 min from $825 See these tours ↓

Tours from Chicago

Choose Your Chicago Tour

Private tours (2)

Small-group tours (4)

Multi-day tours & transfers (1)

Questions about tours from Chicago

Do tours from Chicago include pickup?

Yes. Our tours include pickup and drop-off in Chicago. Your pickup time is confirmed after you book.

How long are day tours from Chicago?

Tours from Chicago last about 6 hrs 30 min – 16 hrs 30 min, depending on the destination.

Are there private and small-group tours from Chicago?

We offer 2 private tours and 4 small-group tours from Chicago. Private tours are just for your party and can be adjusted to your pace.

How much does a day tour from Chicago cost?

Tours from Chicago start from $825 per person. Each tour page shows the live price and availability for your date.

Can you plan a custom tour from Chicago?

Yes. Tell us your dates, group size and interests, and we will plan a private day around you.

Want something different?

Tell us your interests and we'll plan a private day in Chicago around you.

Plan a custom tour

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