Planning a wedding in Chicago? Make the experience unforgettable for your out-of-town guests by organising a full weekend itinerary they’ll love. From iconic attractions to local hotspots, Chicago has something for everyone. So before you go out and book bus transportation for wedding guests, make sure to check out our suggestions for group activities for your wedding weekend.
Friday: Welcome to the Windy City
Kick off your wedding weekend with a warm welcome and a taste of Chicago’s charm.
Afternoon arrival at the hotel – Make your guests feel appreciated by greeting them with welcome bags filled with local snacks, a custom itinerary and CTA cards or shuttle details. Arrange group check-ins at a conveniently located hotel such as the Palmer House, Hyatt Regency or a boutique stay in River North.
Evening welcome dinner or cocktail party – Host an informal get-together at a local venue. Consider:
- RPM Italian or The Dawson for upscale dinners
- Cindy’s Rooftop for drinks with skyline views
- A private room at a restaurant near the hotel for a more intimate vibe
Optional nightcap or neighbourhood stroll – Organise a short walking tour through Millennium Park or along the Chicago Riverwalk for those arriving early and wanting to stretch their legs.
Saturday Morning: Sightseeing with style
Help your guests get the most out of their visit with curated Chicago experiences.
Group breakfast or brunch – Arrange a group reservation at:
- The Bongo Room (Wicker Park) – known for decadent pancakes
- Beatrix (River North) – modern brunch with healthy options
- Wildberry Pancakes (near Millennium Park) – a crowd favourite
Mid-morning bus tour – Charter a private bus and treat guests to a scenic ride through the city. Highlights can include:
- Chicago’s Lakefront and Museum Campus
- Historic neighbourhoods like Hyde Park or Lincoln Park
- Architectural marvels in The Loop and Gold Coast
Alternative Option: Chicago River architecture cruise – A relaxing and informative experience your guests won’t forget. You can pre-book a group outing for added convenience.
Saturday afternoon: Free time with recommendations
Let guests explore while offering helpful ideas to guide their adventures.
Shopping and exploring – Suggest places like:
- The Magnificent Mile for fashion lovers
- Andersonville or Wicker Park for indie boutiques and local flair
- The Art Institute of Chicago for culture and creativity
Foodie suggestions – Provide a list of must-try local spots:
- Deep dish pizza at Giordano’s or Lou Malnati’s
- Chicago-style hot dogs at Portillo’s
- Local coffee and dessert shops like Do-Rite Donuts or Intelligentsia
Tips for transportation – Even if you’re not shuttling all day, offer guests info about ride-sharing apps, L-trains or provide bus transportation for your wedding guests between key locations as needed.
Image of The Bean by Bronisław Dróżka from Pixabay
Saturday evening: The big event
It’s time for the wedding ceremony and reception – make it easy for guests to show up relaxed and ready to celebrate.
Pre-wedding shuttle service – Charter shuttle buses or mini coaches to transport guests from the hotel to the ceremony and reception venue. This ensures punctuality and eliminates the stress of parking or getting lost.
Ceremony and reception ideas – Whether it’s a lakeside venue, urban rooftop or historic church, choose a location with visual wow factor. Chicago favourites include:
- The Rookery Building (classic architecture)
- Galleria Marchetti (garden feel in the city)
- Bridgeport Art Center (industrial-chic elegance)
Afterparty transportation – Keep the celebration going by transporting guests to a nearby bar or lounge for an afterparty. Or return them safely to the hotel with a late-night shuttle.
Sunday: Send-off brunch and goodbyes
Close the weekend with gratitude and one last shared meal.
Farewell brunch options – Organise a group brunch or suggest places guests can visit at their leisure:
- The Publican (West Loop) – communal tables and farm-to-table fare
- Little Goat Diner (by celebrity chef Stephanie Izard)
- The Lobby at the Peninsula Hotel – elegant and refined
Group transportation back to airport – For guests flying out, consider arranging return trips with group transportation – especially if many are leaving around the same time. Chicago bus rentals can simplify this process, especially with luggage in tow.
Thank you notes and parting gifts – Leave guests with a final token of appreciation – a mini box of local chocolates, a framed group photo or a thank you card with a personalised note.
Bonus ideas: Optional add-ons for extra fun
If your guests are staying longer or you want to make your weekend stand out even more, consider adding:
- Friday morning yoga or a spa experience – Help guests unwind with a group session at a local studio or hotel spa.
- Saturday group activity – Host a private workshop – pizza making, mixology class or even a mural tour in Pilsen.
- Sunday walking tour or boat ride – For later flights, organise a light and scenic group activity after brunch.
Top image of The John Hancock Center by guerriernoir from Pixabay
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