Our bride loves St. Patrick’s Day. So naturally, we planned her bachelorette weekend around when the Chicago River turns green. It makes for great pictures.
Vegas, Nashville, Savannah, and Miami were instantly off the table for our group, it’s too common. New Orleans was considered… but Chicago felt like the perfect option. It’s an iconic city with good food, many people in our East Coast group had never been to Chicago before, so it really was the perfect location for us.
Here is our bachelorette itinerary: 3 days in Chicago for 13 people — what worked and tips if you’re considering the same.
Why Chicago Was the Perfect Bachelorette Destination
- Watching the Chicago River turn green is a hella unique experience
- Inexpensive flights from the East Coast
- Iconic city with great nightlife
- Deep-dish pizza
- Marijuana is legal
- Walkable neighborhoods with distinct vibes
- Legendary St. Patrick’s Day energy
Where We Stayed: Old Town Airbnb can sleep 14 people.
Old Town was clutch for logistics. It gave us:
- Easy access to River North, West Loop, and Wrigleyville
- Bars and restaurants within walking distance
- A big space to pregame, recover, and keep 13 people organized
When you have a large group, location is more important than aesthetics, but the Airbnb was still pretty cute.
Day 1: Arrival + Pizza Night (Thursday)
Check-in: 4:00 PM
Goal: Settle in, eat well
- Walked to Curaleaf (0.4 miles from the Airbnb) for our gardener girls
- Ordered delivery for a deep-dish pizza party
- Choose from Lou Malnati’s, Giordano’s, My Pi, or Pequod’s
- About $200 total (~$17 per person)
- My favorite: Pequod’s
Game idea: Order multiple pizzas and do a taste test. Everyone secretly votes on the best. Whoever chooses the same as the bride takes 1 shot; losers take 2 shots.
- Gave time for people to catch up; most hadn’t seen the bride recently. Vibes: Pajamas, wine, joints, and music
- Nearby Old Town bars like Happy Camper were ready for anyone with energy — no pressure to go out
Day 2: Sightseeing, Culture & Dinner (Friday)
Goal: See Chicago and giggle
Morning
- Green mimosas at the Airbnb to commit to the theme early
- Use Blue Curcao or chlorophyll drops to dye them green.
Midday
- Millennium Park for Bean photos – a classic.
- Walk to Navy Pier for more pictures and lunch
- Quick options: Portillo’s, Billy Goat Tavern, or the Navy Pier food court
- Debated tourist options: Skydeck, 360 Observation Deck, or river boat tours. Boat tours lost due to cold weather.
- We went to Skydeck for more great group photos
Afternoon
- Break and regroup back at the Airbnb. Some people stayed out to see Milenium Park, some went back to rest and get ready for the evening
Evening
- Dinner at Beatnik Chicago (West Town)
- Mediterranean cuisine
- ~$60 per person
- Huge hit
Post-dinner drink options (walkable or nearby):
Forbidden Root Brewpub, Beauty Bar, The Vig, Old Town Ale House
We chose Beauty Bar ❤️
More Club options for night owls:
Smartbar, Tao Chicago, Berlin
Day 3: The Shamrock Sh*t Show (Saturday) — St. Patrick’s Day
Goal: Be ridiculous and green
Morning
- Pregame with food, hydration, and layers
- Watch the river dyeing near the Reid Murdoch Building (started around 9 AM)
Late Morning to Afternoon
- Bar crawl and start in River North. Here are the big players:
- Joy District
- Three Dots and a Dash
- Hubbard Inn
- Mother Hubbard’s
- Electric Hotel
Either commit to one bar with ticketed entry or be prepared to bar hop and pivot as lines get long — flexibility required. We chose Point and Feather – a dart bar across from Joy District Chicago – found an empty part of the bar for our group to take over. We found it didn’t matter what bar we chose because our group brought the fun regardless.
More Irish staples:
O’Leary’s Public House, El Hefe, O’Callaghan’s (open until 4 AM)
Evening
- Shift back to Old Town for sit-down food
- Azul
- Old Town Pour House
- AliveOne (happy hour 4–6 PM)
- Wrigleyville crawl for a slightly calmer vibe starting at Moe’s Cantina
For the unhinged to keep going:
Tao, Blind Barber, Disco, Nights & Weekends (West Loop)
Day 4: Checkout & Survival (Sunday)
- Checkout at 11 AM
- No plans. Just hugs and iced coffees.
- But, if some people are still around – maybe go back for the river boat architecture tour, what you didn’t get to on Saturday. It really is beautiful, and is what makes Chicago so special.
Tips for Planning a Chicago Bachelorette Weekend
- Pick neighborhoods wisely: Old Town or River North work best for groups
- Build in downtime: Especially important in cold weather
- Commit to a theme: All parties are better with a theme, and St. Patrick’s Day was built in, and made everything easy and memorable
- Don’t over schedule: Hit the highlights and allow people to opt in or opt out. I actually really wanted to do a brunch reservation, but the group couldn’t rally in time / didn’t want to.
- Pizza night at home > another restaurant reservation
Final Thoughts
Chicago might not be the first city you think of for a bachelorette, but it was great and come with it’s own theme. For us East Coasters – it was very original – especially during St Patricks Day.
Between the food, the neighborhoods, the culture, and the absolute madness of St. Patrick’s Day, it delivered everything we wanted, without forcing anyone into a cliché.