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Chicago Girls’ Weekend: The Itinerary I’d Plan if My Besties Were Visiting!
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items Coming to Chicago for a girls’ weekend? I got youuuuuu. I’m a type A girlie so you don’t have to be—I fully planned out each day so you can just show up, look cute, and know you’re hitting the best (and most popular) spots. This itinerary mixes a lit...
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Friday's Itinerary
Saturday's Itinerary
Friday's Itinerary
FRIDAY: ease into the weekend, but make it ✨aesthetic✨. We’re starting things off with solid food, a little shopping, and cocktails with a view—aka the soft launch before Saturday gets a little unhinged.
1. Brunch! Lux Bar has SUCH good food and their vibe is 100/10. It's one of my favorite places in the city!
LUXBAR
2. Oak Street is just steps from brunch and lined with some of the best luxury stores in the city—think Prada, Hermès, and Chanel. But don’t worry, it’s not just designer. You’ll also find spots like Aritzia and Lululemon, so you can mix high-end win...
Oak Street Chicago
3. Coffee break – you’ve earned it. Shopping is basically cardio, and you’ve got a full day ahead. Time to refuel, reset, and romanticize your iced latte moment before we keep it moving.
Foxtrot Market
3. Right across the street? Chicago’s version of Erewhon (kind of). Okay, maybe that’s a stretch—but people do say it, and the smoothies live up to the hype. It’s the perfect spot to grab some healthy snacks, wellness-y extras, and anything you want ...
Chicago Health Foods
4. Cocktails at LondonHouse rooftop. It’s a classic for a reason—the views are unreal and the drinks don’t disappoint. It’s the kind of place that makes you feel like you’re in the skyline, not just looking at it. And yep, it’s also a hotel (if you’r...
LH Rooftop
5. Dinner at Pizzeria Portofino. If carbs + waterfront views = your love language, this place will ruin you (in the best way). From the cacio e pepe to the wood-fired pizza, everything slaps. And the vibes? Like an Italian summer got dropped right on...
Pizzeria Portofino
6. Gus’ Sip & Dip—for round two (or three) of cocktails. Every drink is $12, and they’re actually so good. The vibe feels old-school in the coolest way—like a throwback bar, but somehow brand new. No reservations (at least for now), so go early o...
Gus' Sip & Dip
7. End the night at Loft 22—where Restoration Hardware meets the club. It’s giving moody lighting, insane design, and music that actually hits. The DJs never miss, the cocktails are solid, and yes—you can absolutely dance here without feeling like yo...
LOFT 22
Saturday's Itinerary
SATURDAY: the main event. Today’s the day to go all in. We’re talking sightseeing, MORE drinks, a little retail therapy, and dinner that lives in your head for weeks. It’s a full itinerary, but don’t worry—I mapped it out like the type A girlie I am,...
1. Chicago Architecture Center River Cruise 🌆 You’ll glide through Chicago’s “river canyon,” passing iconic gems like the Willis Tower, Tribune Tower, and Marina City—while learning the juicy stories behind the skyline. It’s the perfect mid‑day brea...
First Lady - Architectural Tour
1. Not into boats? No problem. Skip the cruise and take a stroll along the Riverwalk instead. You’ll still get incredible views of the skyline—and there are plenty of spots to grab a drink or a bite along the way.
Chicago Riverwalk
2. Next stop: Time Out Market in West Loop. One of just a handful in the world, this spot brings together some of the best food and drink vendors in the city—all under one roof. It’s a great way to sample different flavors without committing to a ful...
Time Out Market Chicago
3. More shopping, obviously. Start with Uncommon James—Kristin Cavallari’s jewelry and lifestyle brand—then hit nearby favorites like Madewell, Free People, Anthropologie, and Mejuri.
Uncommon James
4. Dinner at Aba—Mediterranean, but elevated. This spot is so good it lives rent-free in my head. The menu is incredible (do not skip the whipped feta), and if you can get a table on the patio, do it—it’s straight-up magical. Perfect mix of good food...
Aba
5. Bisous for cocktails—because yes, you can keep drinking. This place serves some of the best cocktails in the city, full stop. The vibe is cool without trying too hard, and their branding? Immaculate. I know, you’re probably thinking, “how much can...
Bisous
6. Keep Bar-hopping, but don’t skip The Vig. West Loop has a ton of solid bars, but The Vig is the one you have to hit. They serve hot cookies at midnight (yes, really), and sometimes a saxophonist or violinist will pop out and start jamming with the...
The VIG West Loop