How to Plan the Ultimate Chicago Bachelorette Weekend a St. Patrick’s Day Twist

Our bride loves St. Patrick’s Day. So naturally, we planned her bachelorette weekend for the weekend when the Chicago River turns green. It makes for great pictures.

Vegas, Nashville, Savannah and Miami were instantly off the table for our bride. New Orleans was considered...but Chicago felt like the perfect option - it's an iconic city, good food, and they're famous for St. Patrick’s Day. Many people in the group had never been to Chicago before, and some had but never partied as an adult.

Here our itinerary for our 3-day Chicago bachelorette for 13 people, what worked, what I’d do again, and tips if you’re considering the same.

Why Chicago Was the Perfect Bachelorette Destination

• Inexpensive flights from the East Coast

• Iconic city, with great nightlight and deep-dish pizza

• Marijuana is legal

• Walkable neighborhoods with distinct vibes

• Legendary St. Patrick’s Day energy

  • Watching the Chicago River turn green is a hella unique experience

    
    

Where We Stayed: Old Town Airbnb that slept 14 people.

Our Airbnb.

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 women organized

  
  

When you have a large group, location was more important than aesthetics, but the airbnb was still pretty cute.

Day 1: Arrival + Pizza Night (Thursday)

• Check-in at 4 PM

• Goal: settle in, eat well, don’t overdo it

• Walked to CuraLeaf (0.4 miles) for essentials for our gardener girls

• Order deliver Deep-dish pizza party. Choose from Lou Malnati’s, Giordano’s, My Pi, and Pequod’s (about $200 total, ~$17 per person) My favorite Pequods.

  • Idea for a game: You order multiple pizzas, and do a taste test and vote, whoever chooses the same as the bride has to take 1 shots, losers take 2 shots.

• Pajamas, wine, joints, and vibes

• Nearby Old Town bars like Happy Camper were ready for anyone with energy, no pressure to go out

• Gives time for people to catch up, most hadn't seen the bride or each other recently

Day 2: Sightseeing, Culture & Dinner (Friday)

Morning:

• Green mimosas at the Airbnb to commit to the theme early - use chlorphyll to dye it, so now we're also being healthy.

• Slow morning to recover from travel and pizza party

  
  

  

Midday:

• Millennium Park for Bean photos

• Walked toward Navy Pier for lunch

• Quick lunch options: Portillo’s, Billy Goat Tavern, Navy Pier food court

• Debated between 2nd tourist option: Skydeck, 360 Observation Deck, and boat tours (boat tours lost due to cold)

• We went to Skydeck for more great group photos.

Afternoon:

• Break and regroup back at the Airbnb. Some people stayed out, some people went back to rest and get ready for evening.

  
  

Evening:

• Dinner at Beatnik Chicago (West Town), Mediterranean cuisine, ~$60 per person. Was a huge hit.

• Post-dinner drinks options that are walkable or nearby: Forbidden Root Brewpub, Beauty Bar, The Vig, Old Town Ale House

• Club options for night owls: Smart Bar, Tao Chicago, Berlin

  
  

Day 3: The Shamrock Sh*t Show (Saturday) — St. Patrick’s Day

Morning:

• Pre-gamed with food, hydration, and layers

• Watched the river dyeing from near the Reid Murdoch Building (started at 9 AM)

  
  

  

Late Morning to Afternoon:

• Bar crawl starting in River North: Joy District, Three Dots and a Dash, Hubbard Inn, Mother Hubbard’s, Electric Hotel

• Either commit to one bar with tickets, or prepare to bar hop and potentially pivo as lines got long —flexibility required.

• Irish staples: O’Leary’s Public House, El Hefe, O’Callaghan’s (open till 4 AM)

Evening:

• Shifted to Old Town for sit-down food at Azul, Old Town Pour House, or AliveOne happy hour (4–6 PM)

• Wrigleyville crawl for a slightly calmer vibe starting at Moe’s Cantina

• For the unhinged: Tao, Blind Barber, Disco, Nights & Weekends (West Loop)

  
  

Day 4: Checkout & Survival (Sunday)

• Checkout at 11 AM

• No plans, just hugs and iced coffees.

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: St. Patrick’s Day made everything easy and super memorable

• Don’t over schedule: Hit the highlights and allow people to opt in or opt out

• 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 good and for us 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.