Chicago gets slept on as a bachelorette destination — but it shouldn't. The city has incredible restaurants, rooftop bars, architecture, lake beaches, and a nightlife scene that rivals any major city. Here's how to do it right.
Where to Stay
River North is your best bet for a bachelorette group. It's walking distance to the best bars and restaurants, close to the Magnificent Mile for daytime shopping, and has the widest selection of multi-bedroom apartments to fit your whole crew.
For a group of 6–10, our River North 3BR and 4BR apartments are perfect — everyone stays together, no splitting up across multiple hotel rooms.
Day 1: Arrive & Explore
- Check in, get settled, hit the grocery store (we recommend Whole Foods on Grand Ave) - Afternoon: Architecture Boat Tour on the Chicago River — genuinely one of the best 90 minutes you'll spend in any city - Evening: Dinner at Maple & Ash (steak, wine, incredible atmosphere) - Night: Rooftop drinks at Raised Bar at the Renaissance
Day 2: Brunch → Activities → Night Out
- Brunch at The Publican or Bavette's Bar & Boeuf - Afternoon: Spa at East Bank Club, or a painting/pottery class if the group is into that - Pre-game at the apartment (save money, have fun, it's part of the tradition) - Dinner: Girl & the Goat or Monteverde - Night: Start at Untitled Supper Club, then move to Sound-Bar or Spybar
What to Book in Advance
- Architecture tour (sells out, especially weekends) - Restaurant reservations (2–3 weeks minimum for the spots above) - The apartment itself — weekends book fast, especially April–October
Need help coordinating? Our concierge team can handle restaurant reservations, decoration setup, and more. Just ask.