Planning a Chicago getaway with your girlfriends? Looking for a fun Chicago itinerary for your next girls’ trip? Or, perhaps you’re planning a Chicago bachelorette trip! Chicago is such a fun spot to explore with friends, so we’ve put together the perfect girls’ weekend in Chicago itinerary. Chicago is full of life, with bars and restaurants galore. The winters get quite chilly (and you can expect some travel delays), but the party does go on, even in the winter! We’d recommend Chicago anytime from April-October for the best weather. No matter when it is, we hope you enjoy your next girls’ trip to the Windy City!

Day 1 of your Chicago Girls’ Weekend

Afternoon: Arrive at O’hare & Get Settled

We always recommend flying into O’hare. Midway is much further from the city! The easiest way to get into the city from the airport is via Uber/Lyft! If you’re trying to decide where to stay in Chicago, check out our Ultimate Guide to Where to Stay in Chicago coming soon to the blog!

Evening: Grab Drinks in West Fulton Market Before Dinner

After you’ve settled in and freshened up, head out to West Fulton Market and start at Federales. Federales is a Mexican restaurant and bar that’s known for its margaritas and tequila shots in ice glasses. Sometimes there’s a line to get in, but it typically moves quickly. The bar area has seating that’s first-come-first-serve, and there’s lots of areas to hang out. Order tequila shots in the ice glasses, and after you take the shot you’ll aim at the bell and try to hit it with your ice glass. It’s a fun first stop, and a great way to kick off a fun girls weekend in Chicago.

If you’re wanting another drink before dinner, check out one of the many West Fulton Market bars. Some of our favorites are La Josie rooftop, Emporium, Time Out Market, and Blind Barbour (speakeasy through a real life barber shop).

Dinner: Grab Dinner at Cabra in West Fulton Market

After you’re done with your opening drinks, walk over to dinner at Cabra, Joe’s Imports, or La Josie! All three of these are great spots for mid-sized groups and have delicious dinner menus. You’ll enjoy yummy food and cocktails at any of these! Each has unique benefits. Cabra is on the rooftop of the Hoxton and boasts beautiful views of the city. Joe’s Imports has a wonderful patio area and delicious Italian dishes. And, finally, La Josie has a first-come-first-serve rooftop that’s cute, or the inside is still great! It features delicious Mexican dishes.

Night: Grab a Nightcap at Recess

Recess is a bar with an indoor area and outdoor area made of shipping containers. It’s a massive space that fills up with young people every night. It’s a super fun area to grab drinks and hang out! They have some fun drinks to share as a group, too.

Day 2 of your Chicago Girls’ Weekend

Morning: Start your day at the Bean

If your group hasn’t been to Millennium Park before, it’s worth a visit to see the Bean in person! Grab a coffee near your hotel, and head out to Millennium Park before it gets too crowded. There’s not too much else around, but it’s a fun and quick stop before brunch.

Morning: Head to Brunch at Beatnik on the River

Walk from the Bean to Beatnik on the River, which is the perfect Instagram-able Chicago brunch spot. Plus, it has some delicious food and brunch cocktails. I love taking groups here because there is a gorgeous view of the Chicago River, and it’s in the perfect location for exploring downtown Chicago afterwards.

Early Afternoon: Walk Along the Chicago Riverwalk & Magnificent Mile Towards 360 Chicago

From Beatnik, you’ll be a able to easily access the Chicago Riverwalk to head towards the Magnificent Mile. The Riverwalk offers a great scenic path for exploring the city. Once you reach the DuSable Bridge, take the stairs up to be higher than the river. You’ll see the Tribune Tower which offers a great overlook with amazing views of the city and river.

From there, you’ll be at the start of the Magnificent Mile. The Magnificent Mile is a stretch of high end shops and a few eateries and exhibits. Even though you just had brunch, it’s worth stopping by the Starbucks Reserve. It’s the world’s largest Starbucks! It has one of the world’s few curved escalators and is four stories tall with a rooftop deck on the top floor. They have delicious pastries, amazing coffee drinks, and delicious alcoholic coffee beverages, too.

Make your way down the Magnificent Mile, and if you haven’t ever been to any of the major Chicago attractions, we recommend checking out 360 Chicago. 360 Chicago is located on the top floor of the John Hancock building. At roughly 1,000 feet above the city, you’ll have an amazing view!

If you’ve already done the Chicago tourist attractions, try heading over to Flight Club after the Mag Mile instead! Flight Club is a fun, upscale spot to play electronic darts. Or, below it is Ace Bounce, a similar vibe spot for playing ping pong.

Afternoon: Take a Chicago Architecture River Cruise

Head back walking from the John Hancock building towards DuSable Bridge where you’ll board the Wendella Boats Sunset Chicago River Cruise. If you have time to spare before the cruise, grab a rooftop drink at LondonHouse. The drinks are quite pricey (~$25 each) and from sunset on there can be a line, but during the day you should have no issues getting up. You’ll want to ask for the open air rooftop, not the indoor rooftop restaurant.

Board the Wendella River Cruise to watch a beautiful Chicago sunset from the Chicago River. Depending on the time of year, and especially if your boat tour takes you into the lake, it can get quite chilly so be prepared. The sunset tour doesn’t have much narration – it’s more of a grab a drink at the bar and sit and chat with friends. If you’re looking for more narration about the city’s history and architecture, be sure you choose a non-sunset tour. We’ve found that sunset tours are perfect for girls’ trips because you can talk all you want without disturbing your neighbors where as on the architecture cruise, you’ll need to be silent!

Night: Grab Dinner along the Chicago Riverwalk

Following the river cruise, walk along the Chicago Riverwalk to dinner at Pizzeria Portifino (the tents in the image above). Or, if you’re feeling like a splurge, book a table at RPM Seafood (just above Pizzeria Portifinio). Both are really delicious and fun options for a group!

Late Night: Grab a Drink at a Chicago Rooftop Bar

Need one more drink before calling it a night? Head over to Raised Rooftop. Raised is on the third floor of the Renaissance Hotel, but because of it’s location, it offers an amazing view despite being on just the third floor. Other rooftop options close by are Cindy’s overlooking Millennium Park and Cerise Rooftop at the top of the Virgin Hotel.

Having inclement weather during your visit? Try visiting Roof at theWit for an enclosed rooftop bar.

Day 3 of your Chicago Girls’ Weekend

Morning: Grab Brunch at Happy Camper Wrigleyville

A trip to Chicago isn’t complete without a visit to Wrigleyville! So, grab a reservation at Happy Camper for a fun boozy brunch before heading out to catch your flight home. If you’re wanting a more mature spot, book a table at Swift and Sons Tavern for a more sophisticated brunch in Wrigleyville. Be sure to walk over to the stadium before or after eating for a quick view of one of the country’s oldest baseball stadiums.

Mid-Day: Explore Lincoln Park

If you have extra time before your flight, either continue exploring Wrigleyville (Deuces and Old Crow are two of our favorite Wrigley bars), or head south towards Lincoln Park for some shopping and living like the locals. There are lots of cute shops and a few breweries like Off Color that we love!

We hope you enjoy your girls’ weekend trip to Chicago! Drop any questions for us in the comments or email us at hello@timeofftravelers.com! And, don’t forget to follow along on Instagram (@timeofftravlers) for more Chicago content!