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
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 The Pacific tours
- 🚐 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.
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.
See these tours ↓
Tours from Chicago
Choose Your Chicago Tour
Private tours (2)
Mackinac Island Private Day Tour from Chicago
Embark on an unforgettable adventure from Chicago to Mackinac Island, where car-free streets, horse-drawn carriages, and Victorian charm await among breathtaking Great Lakes scenery and legendary…
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Small-group tours (2)
Chicago Small Group City Tour
Discover Chicago on an all-inclusive small group city tour with expert guidance, transportation, tickets, and lunch provided. Explore top landmarks and neighborhoods with personalized attention and…
Chicago-Milwaukee Small Group Tour
Indulge in a lavish small group day trip from Chicago to Milwaukee, featuring guided tours of iconic landmarks, exclusive Miller Brewery tastings, and seamless luxury transport…
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More day tours (2)
One Day Galena and Dubuque Tour from Chicago
Indulge in an exquisite day trip from Chicago, discovering the elegance of Dubuque's riverside charm and Galena's historic grandeur, complete with exclusive visits and breathtaking vistas…
Chicago to Mackinac Island Scenic Tour
This tour from Chicago to Mackinac Island offers a serene getaway featuring scenic Great Lakes travel, car-free Victorian charm, historic sites like Fort Mackinac, and local…
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Multi-day tours & transfers (1)
2 Day Private Tour Chicago to Mackinac Island Exploration
Embark on an epic journey from Chicago to Mackinac Island, where horse-drawn carriages, breathtaking limestone arches, historic forts, and legendary fudge await in a car-free paradise…
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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 2 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.
Tell us your interests and we'll plan a private day in Chicago around you.
