From wine bars to outlet malls to kayak tours — find group travel ideas for a girl's getaway to Chicago

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Encourage your clients to gather their friends and plan a few days of excitement in Chicago. With so many options for dining, nightlife, dance clubs, shopping, spas, theater and culture, the opportunities for a fantastic girls getaway are endless.



The Bedford
1216 W. Division St., Chicago
Located in a historic landmark bank space, complete with cocktails in “the vault,” and inspired by the supper club experience of a bygone era, The Bedford serves up modern American cuisine.

Cafe Ba-Ba-Reeba
2024 N. Halsted St., Chicago
Groups will love the lively Mediterranean atmosphere and authentic Spanish cuisine at this Lincoln Park restaurant, featuring tapas, pintxos, paella and sangria. 

Castaways Bar & Grill
1603 N. Lake Shore Dr., Chicago
Overlooking Lake Michigan with incredible views of the city, Castaways is a casual dining spot with a prime location on the beach. Guests can enjoy tantalizing appetizers, sandwiches, fresh salads and refreshing desserts. And did we mention cool beverages?  Choose from piña coladas, margaritas, daiquiris and cold draft beer. For groups, consider renting a cabana.  

Japonais by Morimoto
600 W. Chicago Ave., Chicago
Japonais offers exceptional contemporary Japanese cuisine and sushi in an extraordinary setting. Modern day Japan meets European elegance in this trendsetting space. Traditional sushi and contemporary entrees include filet mignon, broiled lobster and smoked duck. Casual lounge seating and private dining areas are available for groups and parties.

Lou Malnati’s Pizzeria
Various Locations
Considered the oldest family name in Chicago pizza, Lou Malnati's has stayed true to the original Chicago style deep-dish pizza recipe first created in the 1950's. Plan a casual girls night at one of these pizzeria locations, famous for buttery crust, sweet and tangy tomatoes, gooey mozzarella cheese and perfectly seasoned sausage.

Mercadito Chicago
108 W. Kinzie St., Chicago
Expertly blending traditional Mexico with creative interpretations of local and seasonal ingredients is the inspiration behind Mercadito restaurants. Spanish for “little market,” Mercadito is modeled after Mexican markets, serving up colorful tacos, flavorful guacamoles, innovative ceviches and creative cocktails.

Odyssey Cruises
Navy Pier, 600 E. Grand Ave., Chicago
Groups can enjoy brunch, lunch or dinner with spectacular views on a cruise along Lake Michigan. Climate controlled decks make for a comfortable setting, while cityscape views and gourmet meal options round out the experience. 

Summer House Santa Monica
1954 N. Halsted St., Chicago
California-influenced New American fare is paired with sustainable wines and a relaxed, beach-inspired vibe at this welcoming eatery. Locally sourced ingredients are used whenever possible.

Sunda New Asian
110 W. Illinois, Chicago
Guests can enjoy both private and non-private areas in this hip, celebrity-touted River North restaurant, where Asian fusion eclectic cuisine is served in an inviting, modern atmosphere.

Untitled Supper Club
111 W. Kinzie St., Chicago
Visitors may have a hard time seeing this establishment from the street, but look hard – it’s worth it. This speakeasy-style supper club offers dinner and nightly live entertainment, ranging from bluegrass to jazz, and it boasts more than 400 American whiskeys, craft cocktails, beers and an array of wines. 



Tastebud Food Tours
Various Locations
From deep dish pizza to Chicago-style hot dogs, visiting foodies can experience the best of Chicago's iconic dishes on these 3-hour guided tours. Tastebud Food Tours even offers private tour options, perfect for larger groups who want to sample only-in-Chicago foods in their historic settings.

Chicago Dine-Around
Various Locations
Visitors can embark on a unique adventure to Chicago's best restaurants with these dining tours. During the Progressive Dining Tour, guests travel around Chicago in a stylish coach bus to enjoy hors d'oeuvres served at the first restaurant, the main course at a second restaurant and dessert at a third restaurant. The tour offers a unique, fun and exciting way to experience different Chicago restaurants, interact with other guests and tour the city in one memorable evening.

Chicago Food Planet Tours
Various Locations
Plan a food tasting and cultural walking tour specializing in combining delicious food and drink tastings with some serious fun in Chicago’s most delicious, off-the-beaten-path neighborhoods. Rated the No. 1 Food Tour by TripAdvisor with over 1,000 reviews, these narrated food tours include numerous food tastings from specialty food stores and ethnic eateries.



Bottle & Bottega
Various Locations
For groups who love art, wine and even a little creativity, this interactive experience is sure to be a hit. Guests can sip wine while painting their own masterpiece and enjoying time with friends. For larger groups, book a private party.

43 E. Ohio St., Chicago
Your clients can learn fun cooking techniques and food knowledge alongside friends when you sign them up for a hands-on class at Eataly. From informative cheese classes to hands-on pasta workshops to wine tasting panels, these classes offer plenty of insight and excitement for foodies. 

KOVAL Distillery
5121 N. Ravenswood Ave., Chicago
For libation lovers, plan a trip to KOVAL Distillery for a day of behind-the-scenes activities. As Chicago’s first distillery since the mid-1800s, this family-owned craft distillery creates a variety of organic spirits and liqueurs. Visitors can take a tour every Wednesday, Saturday or Sunday and sign up for a variety of classes, from hands-on cocktail mixology classes to informative seminars on the history of American whiskey. Private tours for large groups are available.

Laudi Vidni
1007 W. Armitage Ave., Chicago
Located in the historic Lincoln Park neighborhood, this upscale design studio offers visitors the opportunity to design their own handbags. Visitors can peruse sample bags, get a feel for an array of leather swatches and design their own personal accessory – all while enjoying chilled champagne.

Punch House
1227 W. 18th St., Chicago
At the casual Punch House, groups can make their own punch and learn about the history of this party-friendly cocktail – all while getting a first-hand taste of this delicious concoction. After the event, your clients can stick around for more delicious cocktail and casual – yet gourmet – pub fare, such as lobster rolls, stuffed pretzels and beef fat frites.



Buddy Guy's Legends
700 S. Wabash, Chicago
For a night of old-school blues in a Chicago institution, plan a night out at Buddy Guy's Legends, one of the city’s true cultural landmarks. Owned by Rock and Roll Hall of Famer Buddy Guy, this venue has hosted some of the best local and national blues bands seven nights a week for 20 years. Visitors can enjoy a full menu of authentic Cajun fare along with an authentic taste of Chicago blues.

City Winery
1200 W. Randolph St., Chicago
For wine lovers, this fully functioning winery in Chicago is a must-visit destination. Offering intimate concerts, food and wine classes, weekend brunches and a restaurant touting sophisticated Mediterranean cuisine and an award-winning wine list with more than 400 unique producers, groups will love this wine-centric locale.

House ­of Blues
329 N. Dearborn St., Chicago
Chicago's premier restaurant and concert venue is a unique setting for a night out. The soaring splendor of a European Opera House combined with the down-home aura of a juke-joint make House of Blues a wonderfully unique entertainment experience for a girls’ night out. 

Howl at the Moon
26 W. Hubbard St., Chicago
Howl at the Moon is a live music venue providing dueling piano show entertainment seven per week. Perfect for groups, this singing and dancing interactive form of entertainment promises a fun, lively night out.

Paris Club/Studio Paris Nightclub
59 W. Hubbard St., Chicago
For a night of dining and dancing, this is the spot. This modern French restaurant, located in the heart of Chicago's nightlife district, offers celebrated French classics in an upscale environment. Visitors can have dinner on the main level and then head upstairs for an amazing club scene with big-name DJs, dancing and possibly even a celebrity sighting.

ROOF on theWit
201 N. State St., Chicago
Gal pals can party it up 27 stories above the city on this cool rooftop bar with a fully retractable roof, which makes the destination great any time of year. DJs spin everything from bossa nova to house music, keeping the dance floor moving until early in the morning. Birthday party and bachelorette party packages are available.

The Second City
1616 N. Wells St., Chicago
What's better than an evening filled with laughter? Groups can enjoy a Chicago institution (and a rollicking good time!) at a Chicago-style improv and sketch comedy performance by The Second City.



Bike and Roll Chicago
Various Locations
Plan for a fun, active adventure by renting a large quadcycle. Visitors can tour the 18-mile Lakefront Trail alongside Lake Michigan on a spectacular four-wheeled, canopy-covered quadcycle. Visit Bike and Roll at Navy Pier or Millennium Park – bikes are first come, first served.

Shoreline Water Taxi
Various Locations
Water taxis are a fun way to see the river and lakefront from May through September. Shoreline’s routes carry passengers from the Willis Tower to Michigan Avenue and Navy Pier on the river; and between the Shedd Aquarium and Navy Pier on the lake.

950 N. Kingsbury St., Chicago
Get groups out on the water with a guided kayak tour on the Chicago River. Active visitors will love the chance to get some fresh air and see the Chicago skyline from an exciting vantage point.  



Chicago Premium Outlets
1650 Premium Outlets Blvd., Aurora, IL
With 120 stores, this is a true bargain hunter's haven. Shoppers will find impressive savings of 25 percent to 65 percent every day from leading designers and name brands including Ann Taylor Factory Store, Banana Republic Factory Store, Brooks Brothers Factory Store, Coach, Elie Tahari, Giorgio Armani, Kate Spade New York, Lacoste, Michael Kors and more.

Fashion Outlets Chicago
5220 Fashion Outlets Way, Ste. 230, Rosemont, IL
This outlet mall is located in Rosemont, Illinois near O’Hare Airport and is accessible via the Blue Line CTA train, as well as daily shuttles from The Magnificent Mile. Shoppers can enjoy savings of up to 75 percent off at more than 130 outlet stores, including the likes of All Saints, Prada, Saks, Tory Burch and Hugo Boss.

The Magnificent Mile
N. Michigan Ave., Chicago
Send your clients loose on The Magnificent Mile, where more than 450 retail stores dot North Michigan Avenue and the surrounding area. From Cartier and Louis Vuitton to GAP and H&M, this retail stretch truly is a shopper’s paradise.

Lincoln Park
Wonderful boutiques, restaurants and salons abound on Armitage Avenue, Halsted Street and Webster Avenue, located in the heart of Lincoln Park. This historic Chicago area is considered one of the city’s most desirable neighborhoods due to its charming tree-lined streets, Victorian row houses and unbeatable shopping and dining.

Oak Street
E. Oak St., Chicago
Located on the north side of The Magnificent Mile, Oak Street establishes its own retail glory as the home to many luxury brands such as Hermes, Barneys New York, Jimmy Choo, Prada, Kate Spade and Lanvin, as well as private designer showrooms.

State Street
N. State St., Chicago
This retail-dense thoroughfare includes the modern Block Thirty Seven shopping, dining and entertainment area, as well as the historic Macy's on State Street, featuring an unparalleled merchandise selection, five unique restaurants and architectural icons including the Great Clocks and the renowned Tiffany ceiling. 

Wicker Park/Bucktown
Off-the-beaten path vintage and thrift-type shops, airy gallery style showrooms and cozy urban boutiques help shopping take on a special feel in this vibrant and youthful neighborhood of Chicago. Plan a day of shopping in this trendy area.



Bliss Spa at W Chicago Lakeshore
644 N. Lake Shore Dr., Chicago
Groups looking for pure bliss will find it at Bliss Spa, where movie-while-you-manicure stations, sensational spa treatments and posh surrounding create a refreshing an rejuvenating experience, located just steps from the bustle of The Magnificent Mile. 

The Peninsula Spa by Espa
108 E. Superior St., Chicago
The Peninsula Hotel offers topnotch accommodations with luxurious pampering to match. The Peninsula Spa by Espa is famous for its shoulder melting massages and a jaw-dropping lap pool. Plan some relaxation time for girl friends looking to unwind.

The Spa at Trump International Hotel & Tower Chicago
401 N. Wabash Ave., Chicago
Luxury awaits at this downtown Chicago day spa, where a calming lineup of signature treatments feature precious gem-infused oils and renowned products such as Kate Somerville skin care. Guests also can enjoy the panoramic views of the Chicago River from the on-site health club. 

Waldorf Astoria Spa & Health Club
11 E. Walton, Chicago
This expansive health and wellness center inside the Waldorf Astoria Chicago hotel features a wide-ranging menu of personalized services as well as amenities such as a mosaic tiled pool, whirlpool tubs, dry saunas and eucalyptus steam rooms, as well as a fitness facility complete with a Pilates and Gyrotonics studio. It’s easy for groups to find plenty of ways to relax and rejuvenate.

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