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Group-Friendly Experiences in Old Town, Chicago IL | Book with Varoom

You can enjoy live comedy at The Second City and wander the historic Old Town Triangle area in Chicago, Illinois, USA, with boutique shops, cafés, and photo-worthy architecture for Group-Friendly Events. In Old Town/Chicago, you’ll easily arrange tours, workshops, and family-friendly experiences along the waterfront near iconic sights like Millennium Park and Navy Pier, making planning your multi-day or day-long event simple and memorable.

Discover the charm of Old Town, a neighborhood in Chicago, Illinois, USA, where you can wander brick-paved streets, pop into art galleries, and enjoy a mix of dining and live entertainment. In this destination, you’ll find iconic landmarks and experiences that suit every group, from comedy at The Second City to strolling by historic storefronts in the Old Town Triangle Historic District and catching ambient spots for a relaxed evening. The area also invites architecture lovers and families to explore nearby green spaces and kid-friendly venues, while guided tours and workshops reveal local culture and design. Here, you’ll feel the pulse of the city through convenient, Group-Friendly activities and memorable shows, with options that keep your plans simple and seamless as you book stays aligned with your itinerary.

Activities

Top Group-Friendly in Old Town

Chicago River Architecture: History and Sightseeing Cruise
Chicago River Architecture: History and Sightseeing Cruise
10
Excellent
16066 Reviews
5-Star Rating Recommendation
From
US $40Per Person
Reserve
Medieval Torture Museum Ticket with Audio Guide and Ghost Hunting
Medieval Torture Museum Ticket with Audio Guide and Ghost Hunting
10
Excellent
1030 Reviews
5-Star Rating Recommendation
From
US $51Per Person
Reserve
Chicago Food Tour: Deep Dish Pizza, Beer, Brownies, and More
Chicago Food Tour: Deep Dish Pizza, Beer, Brownies, and More
10
Excellent
2075 Reviews
5-Star Rating Recommendation
From
US $84Per Person
Reserve
Chicago Architecture Boat Tour
Chicago Architecture Boat Tour
10
Excellent
1649 Reviews
5-Star Rating Recommendation
From
US $37Per Person
Reserve
Chicago: Interior Architecture Walking Tour Inside the Loop
Chicago: Interior Architecture Walking Tour Inside the Loop
10
Excellent
1613 Reviews
5-Star Rating Recommendation
From
US $35Per Person
Reserve
Chicago Downtown Donut Walking and Tasting Dessert Tour
Chicago Downtown Donut Walking and Tasting Dessert Tour
10
Excellent
1418 Reviews
5-Star Rating Recommendation
From
US $70Per Person
Reserve
Chicago: Small-Group Food, History, and Architecture Tour
Chicago: Small-Group Food, History, and Architecture Tour
10
Excellent
1232 Reviews
5-Star Rating Recommendation
From
US $99Per Person
Reserve
Chicago Medieval Torture Museum Tickets and Audio Guide
Chicago Medieval Torture Museum Tickets and Audio Guide
10
Excellent
1025 Reviews
5-Star Rating Recommendation
From
US $51Per Person
Reserve
Chicago Loop Small-Group or Private Food and Walking Tour
Chicago Loop Small-Group or Private Food and Walking Tour
10
Excellent
911 Reviews
5-Star Rating Recommendation
From
US $84Per Person
Reserve
Chicago Highlights Bike Tour with Classic Foods and Craft Beer
Chicago Highlights Bike Tour with Classic Foods and Craft Beer
10
Excellent
739 Reviews
5-Star Rating Recommendation
From
US $88Per Person
Reserve
Chicago Small-Group Tour With Optional Architecture Cruise
Chicago Small-Group Tour With Optional Architecture Cruise
10
Excellent
719 Reviews
5-Star Rating Recommendation
From
US $49Per Person
Reserve
Chicago City Small-Group Minibus Tour
Chicago City Small-Group Minibus Tour
10
Excellent
568 Reviews
5-Star Rating Recommendation
From
US $49Per Person
Reserve
Find A Tour In Old Town

From sightseeing to restaurants
there’s plenty of things to do in Old Town

Whether you love exploring landmarks or tasting local cuisine, you’ll find endless adventures here.

Most popular tours in Old Town

See all Tours in Old Town
Chicago River 90-Minute Architecture Tour

Chicago River 90-Minute Architecture Tour

9
Excellent
10059 Reviews
5-Star Rating Recommendation
From
US $45Per Person
Reserve
Chicago River Narrated Architecture Indoor-Outdoor Boat Tour

Chicago River Narrated Architecture Indoor-Outdoor Boat Tour

9
Excellent
9980 Reviews
5-Star Rating Recommendation
From
US $44Per Person
Reserve
Chicago Crime and Mob Bus Tour

Chicago Crime and Mob Bus Tour

9
Excellent
3327 Reviews
5-Star Rating Recommendation
From
US $49Per Person
Reserve
Chicago: Criminals, Mobsters, and Gangsters Bus History Tour

Chicago: Criminals, Mobsters, and Gangsters Bus History Tour

9
Excellent
3310 Reviews
5-Star Rating Recommendation
From
US $41Per Person
Reserve
Chicago River 45-Minute Architecture Tour from Magnificent Mile

Chicago River 45-Minute Architecture Tour from Magnificent Mile

9
Excellent
3188 Reviews
5-Star Rating Recommendation
From
US $28Per Person
Reserve
Chicago Lake and River Architecture Tour

Chicago Lake and River Architecture Tour

9
Excellent
2333 Reviews
5-Star Rating Recommendation
From
US $45Per Person
Reserve
Skydeck Chicago: Entry Ticket

Skydeck Chicago: Entry Ticket

9
Excellent
2290 Reviews
5-Star Rating Recommendation
From
US $42Per Person
Reserve
Chicago Hop-On Hop-Off Sightseeing Tour by Open-top Bus

Chicago Hop-On Hop-Off Sightseeing Tour by Open-top Bus

8
Excellent
2256 Reviews
4-Star Rating Recommendation
From
US $49Per Person
Reserve
Chicago Hop-On Hop-Off Big Bus Tour

Chicago Hop-On Hop-Off Big Bus Tour

8
Excellent
2240 Reviews
4-Star Rating Recommendation
From
US $53Per Person
Reserve
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

9
Excellent
1833 Reviews
5-Star Rating Recommendation
From
US $44Per Person
Reserve
Chicago: Skydeck Chicago at the Willis Tower Admission Ticket

Chicago: Skydeck Chicago at the Willis Tower Admission Ticket

9
Excellent
1826 Reviews
5-Star Rating Recommendation
From
US $44Per Person
Reserve
Lake Michigan Sunset Cruise in Chicago

Lake Michigan Sunset Cruise in Chicago

9
Excellent
1555 Reviews
5-Star Rating Recommendation
From
US $45Per Person
Reserve
See all Tours in Old Town

Other tours in Old Town

Chicago Architecture River Cruise
Chicago Architecture River Cruise
10
Excellent
16151 Reviews
5-Star Rating Recommendation
From
US $39Per Person
Reserve
Chicago Architecture Center River Cruise aboard First Lady
Chicago Architecture Center River Cruise aboard First Lady
10
Excellent
5991 Reviews
5-Star Rating Recommendation
From
US $57Per Person
Reserve
Chicago Favorites Ultimate Food and Walking Tour
Chicago Favorites Ultimate Food and Walking Tour
10
Excellent
2099 Reviews
5-Star Rating Recommendation
From
US $85Per Person
Reserve
Chicago River 90-Minute Architecture Boat Tour
Chicago River 90-Minute Architecture Boat Tour
10
Excellent
1659 Reviews
5-Star Rating Recommendation
From
US $37Per Person
Reserve
Original Chicago Architecture Interiors Tour: Dazzling Interiors
Original Chicago Architecture Interiors Tour: Dazzling Interiors
10
Excellent
1640 Reviews
5-Star Rating Recommendation
From
US $35Per Person
Reserve
Delicious Donuts & City Sights: Chicago's Original Donut Tour
Delicious Donuts & City Sights: Chicago's Original Donut Tour
10
Excellent
1432 Reviews
5-Star Rating Recommendation
From
US $70Per Person
Reserve
Chicago in a Day Walking Tour: Food, History & Architecture
Chicago in a Day Walking Tour: Food, History & Architecture
10
Excellent
1240 Reviews
5-Star Rating Recommendation
From
US $101Per Person
Reserve
Chicago Food Tour: 6 Dishes with Deep Dish Pizza & Beef Sandwich
Chicago Food Tour: 6 Dishes with Deep Dish Pizza & Beef Sandwich
10
Excellent
918 Reviews
5-Star Rating Recommendation
From
US $85Per Person
Reserve
Chicago Bike & Classic Food Tour: Bikes, Bites & Views - Adults
Chicago Bike & Classic Food Tour: Bikes, Bites & Views - Adults
10
Excellent
742 Reviews
5-Star Rating Recommendation
From
US $89Per Person
Reserve
Chicago Murder Mystery and Sightseeing Walking Tour
Chicago Murder Mystery and Sightseeing Walking Tour
10
Excellent
738 Reviews
5-Star Rating Recommendation
From
US $35Per Person
Reserve
Chicago Murder Mystery Tour
Chicago Murder Mystery Tour
10
Excellent
738 Reviews
5-Star Rating Recommendation
From
US $35Per Person
Reserve
Chicago City Tour with Architecture River Cruise Option
Chicago City Tour with Architecture River Cruise Option
10
Excellent
720 Reviews
5-Star Rating Recommendation
From
US $50Per Person
Reserve
Show all Tours in Old Town

Top-rated places to stay near Old Town

Discover top-rated, Group-Friendly stays near Old Town, Chicago, in this area, where convenient access to Events meets comfortable, stylish lodging.
Here you’ll find accommodations tailored for Art & Culture, Tours & Sightseeing, and family-friendly gatherings, perfect for multi-day or single-event plans in the region.
From easy proximity to venues to welcoming spaces for teams and groups, these stays make booking in this destination seamless with Varoom.

Old Town
Old Town88+ Properties
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Apartment
Archways at the Lincoln Park Zoo 2bed/2ba
Map-icon
like-icon10.0
Exceptional
(5 Reviews)
2 Bedrooms 2 Baths 6 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
US $497/Night 7 Nights - US $3,479
View Deal
star-icons-4
Apartment
MTM Fully Furnished Rental in Old Town - 2 beds
Map-icon
like-icon10.0
Exceptional
(1 Review)
2 Bedrooms 1 Bath 5 Guests 947.22 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Air Conditioner
    Air Conditioner
More amenities
US $90/Night 7 Nights - US $630
View Deal
star-icons-3
Bed & Breakfast
The Sono Chicago
Map-icon
like-icon10.0
Exceptional
(511 Reviews)
1 Bedroom 1 Bath
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $187/Night 7 Nights - US $1,307
View Deal
Apartment
Family Friendly 2 Bedroom Full Kitchen Free Laundry Work Space
Map-icon
like-icon10.0
Exceptional
(3 Reviews)
2 Bedrooms 1 Bath 5 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Kitchen
    Kitchen
More amenities
US $604/Night 7 Nights - US $4,225
View Deal
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Know more about Old Town

Cancellation terms vary by rate and dates, and are specified on the listing. Review the listing’s cancellation details and contact the host if you need clarification or to discuss flexible options for your group.
On-site event possibilities and associated rules are defined in the listing. Review the house rules and event allowances, then contact the host to confirm permitted sizes, noise levels, and any required permissions.
Parking options and transit accessibility are described in the listing. Review the details for Group-Friendly transport, nearby parking rules, and walking distances to popular spots, then plan with the host if you have specific arrival times.
Minimum stay and included Services (such as linens, utilities, or on-site amenities) are specified on the listing page. For extended groups, confirm any discounts or special terms directly with the host.
Capacity, bed configurations, and Group-Friendly amenities are listed for your chosen stay. Check the listing for exact numbers and supported features, and reach out to the host with any special requests related to your group.
The listing outlines standard check-in/out times and the method (such as self-check-in). It also lists safety features and any required security steps. For special arrival needs, coordinate with the host in advance.
Some listings offer add-ons or can coordinate experiences through the host. Check the listing for available options and contact the host to discuss dates, pricing, and any equipment or space needs.
Accessibility notes and safety details are provided in the listing. If your group includes guests with specific needs, contact the host to confirm accommodations and any possible adjustments before booking.