Valentine’s Day isn’t just for couples—it’s also the perfect time to celebrate friendships with Galentine’s Day! Whether you’re planning a romantic evening for two, a group date night, or a fun outing with your best friends, a private trolley rental offers a unique way to experience Chicago in February.

With enclosed, heated trolleys, you can explore the city without worrying about the cold, making it the perfect winter transportation for dinner dates, bar crawls, sightseeing, or a festive Galentine’s adventure. Here are some great ways to celebrate this season of love—trolley-style!

1. Valentine’s Day Trolley Date Night in Chicago

Forget the traditional dinner-and-movie routine—make Valentine’s Day unforgettable with a trolley ride through Chicago’s most romantic spots!

Start with Drinks & a Scenic Ride

Kick off your evening by toasting with champagne onboard your trolley before heading to a sky-high cocktail bar or a cozy lounge. A first stop:

Three Dots and a Dash – A fun tiki bar hidden behind an alley, perfect for couples who love craft cocktails.

📍 435 N Clark St | https://www.threedotschicago.com/

A Romantic Dinner Stop

After enjoying the ride, arrive in style at one of Chicago’s top romantic restaurants:

Geja’s Café – One of the city’s most romantic spots, offering fondue dinners by candlelight.
- 📍 340 W Armitage Ave | https://gejascafe.com/
Gibsons Italia – Upscale steak & Italian fare with gorgeous riverfront views.
- 📍 233 N Canal St | https://www.gibsonsitalia.com/

End with a Classic Chicago Experience

Wrap up the night with a ride past Chicago’s most iconic landmarks, including:

The Chicago Riverwalk – Perfect for a romantic stroll along the water.
Navy Pier’s Centennial Wheel – Enjoy the skyline views from a private gondola.
- 📍 600 E Grand Ave | https://navypier.org/attractions/centennial-wheel/

A private trolley makes the night even more special—no waiting for rides, no parking stress, just a smooth ride from one destination to the next.

2. Galentine’s Day Trolley Tour: Brunch, Bars & Fun with Friends

February is the perfect time to round up your best friends for a Galentine’s Day celebration! Whether you’re planning a brunch-and-bubbles tour, a boutique shopping crawl, or a night of dancing, a trolley keeps everyone together while adding a festive touch.

Brunch & Mimosas to Kick Off the Day

Start the fun with a trolley ride to one of Chicago’s best brunch spots:

Hampton Social – River North – Rosé all day vibes with seafood and great cocktails.
- 📍 353 W Hubbard St | https://www.thehamptonsocial.com/
Beatrix – Fulton Market – Cozy brunch with pastries, coffee, and bottomless mimosas.
- 📍 834 W Fulton Market | https://www.beatrixrestaurants.com/

Hit the Best Bars & Lounges

After brunch, bar-hop through Chicago’s best cocktail bars with your private trolley:

The Aviary – Inventive cocktails served in a swanky setting.
- 📍 955 W Fulton Market | https://www.theaviary.com/
Celeste – Chic rooftop bar & dance lounge in River North.
- 📍 111 W Hubbard St | https://www.celestechicago.com/

Fun Group Activities Along the Way

Make it a full Galentine’s adventure with stops at:

Punch Bowl Social – Bowling, karaoke, arcade games, and cocktails—all in one place!
- 📍 310 N Green St | https://www.punchbowlsocial.com/location/chicago/
The Second City – Laugh the night away at Chicago’s legendary comedy club.
- 📍 1616 N Wells St | https://www.secondcity.com/

Why a Trolley is the Best Way to Celebrate

✔ Enclosed & Heated – Stay warm while hopping between stops.
✔ No Waiting for Rides – Keep the night moving without delays.
✔ BYOB-Friendly – Bring champagne or cocktails to enjoy onboard.
✔ Fits Groups of All Sizes – Perfect for couples, double dates, or big friend groups.

Ready to plan your Valentine’s or Galentine’s celebration? Book a private trolley and make it a night to remember!