Chicago, Illinois

The Windy City offers a history of architecture, crime and dirty politics. It is the home of both the Bears and the Cubs not to mention Second City comedy shows, deep-dish pizza, beer, outdoor festivals and farmer's daughters.

Of course, there is plenty to see in Chicago such as the famous Water Tower, the Willis Tower (formerly the Sears Tower) and Wrigley Field. If you look around Grant Park, you can even find Buckingham Fountain (famous for being the opening shot of the title sequence for television's "Married, With Children").

Chicago also has an impressive night life with a myriad of bars, clubs and restaurants. With the right luck, one can make the Windy City even windier.

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New York City is comprised of five boroughs which are home to some of the world's most recognizable landmarks and attractions.

From The Empire State Building and Times Square to Central Park and The Metropolitan Museum of Art, Manhattan packs more legendary icons into one compact area than any other place on Earth; and that's to say nothing of the City's four other boroughs—The Bronx, Brooklyn, Queens and Staten Island—each of which contains its own list of must-see attractions.

With so much to see and do, a trip to New York City may seem a little overwhelming. To help, we've rounded up attractions, hotels, bars and venues that belong on any bachelor's must-see and must-do list.

Our Top Picks !

  • Drake Hotel$$$$

    140 East Walton Pl.

    Despite a lack of street parking in the vicinity, the centrally located Drake Hotel can meet all your travel needs. With amenities like marble bathrooms and four eateries in the hotel, the only thing lacking might be an available room.

  • Ritz Carlton$$$$$

    160 E. Pearson St.

    This particular Ritz-Carlton is owned by the Four Seasons chain and combines elegance with utility. The hotel boasts amenities such as a minibar, slippers and bathrobes for guests. Take in the views from the hotel’s high vantage point!

  • Hotel Palomar $$

    505 North State St.

    With its own rooftop terrace and a free hotel Happy Hour, the Hotel Palomar offers a great location to host a bachelor party. The luxury-level rooms at below-luxury prices allow a group to enjoy food and drink at the Sable Kitchen there.

  • Peninsula$$$$$

    108 East Superior St.

    Modern décor and a Far Eastern flair permeate the Peninsula Hotel. Located across from Chicago’s historic Water Tower, guests can enjoy the complimentary spa and fitness center or simply chill out in the room with mini-bar, TV and Internet.

  • Hyatt Regency$$$

    151 E. Wacker Drive

    This humongous hotel hosts over 2,000 rooms and has cheaper rates to prove it. Your bachelor party will still have decent amenities and a more reliable experience without spending a whole paycheck. Gold Passport members get free Internet.

  • Trump International$$$$$

    401 N. Wabash Ave.

    As ostentatious as the man himself, Trump International Hotel rises up above the Chicago River at the South end of Miracle Mile. It boasts luxuries both usual and unusual such as a spa, great city views, room fireplaces and even kitchens.

  • Hotel Allegro$$$

    171 W. Randolph St.

    Located in Chicago’s Loop, the Allegro boasts a bi-level lobby and eclectic décor and tiny rooms, even for Chicago (book a suite for more space). Since it’s a Klimpton, you can scour the Internet for special passwords to get secret prizes.

  • Hotel Sax$$$

    333 N. Dearborn St.

    The Hotel Sax carries a cool boutique vibe to go along with the central location and the fantastic drinking spot that is the Crimson Lounge (or catch the House of Blues next door). You can even play video games on the sixth floor.

  • The Wit$$$$

    201 N. State St.

    The Wit is a funky hotel that would be mistaken for a rowdy cousin of the W than in fact one of the DoubleTree chain of hotels. Using a strange combination of Miami décor and Los Angeles party scene, it offers amenities like a rooftop view.

  • The W Hotel$$$

    644 N. Lake Shore Dr.

    With Navy Pier on one side and the city of Chicago on the other, the W hotel in Chicago offers a well-located bachelor party headquarters. It possesses a cool vibe, a good bar and a respectful staff. As a bonus, the W offers a lake view.

  • Violet Hour $$$

    1520 N Damen Ave

    When you see a line of people waiting outside a wall with graffitti on it, you've found the Violet Hour. A slick design houses a dimly lit space when patrons suck specialized cocktails at all hours. It's a place you want to go to impress.

  • Signature Lounge at the 96th $$$

    875 N Michigan Ave

    The first thing everyone notices about the Signature Lounge is the spectacular city vistas from its windows. While drinks are expensive and there is a line for the elevator, the view is worth the time and expense. Warning: many tourists.

  • Green Mill $$

    4802 N Broadway St

    The Green Mill offers the finest jazz in the city to go with that drink you're having. Formerly owned by Al Capone way back when, this bar offers inexpensive drinks and street parking to go with the music. Check the walls for its history.

  • Rebar $$$

    401 N Wabash Ave

    Located at the Trump Hotel, you don't go to this bar to save money. The neo-Japanese atmosphere and the spectacular views of the Chicago River and Michigan Ave. Bridge make the drink prices worth it. Food is served as well (good sushi).

  • Webster's Wine Bar $$

    1480 W Webster Ave

    If you're looking for a casual bar with candles on the tables, Webster's could be for you. They also serve such complimentary foods to wine as appetizers and tapas. Beware the crowds on weekends. However, it's a good place to take a date.

  • Suite Lounge $$

    1446 N Wells St

    A great atmosphere and friendly staff make the Suite Lounge a pleasurable experience. Valet service is available, music plays freely for dancing and drinks are reasonably priced. The only negative is that the place tends to get crowded.


    504 N Wells St

    While Sushisamba is known mostly as a sushi restaurant, it's also known as a bar. The cocktails are complimentary to the sushi platters that the patrons eat. Atmosphere is generally friendly. Good place for a large group of people.

  • The Tasting Room $$

    1415 W Randolph St

    The Tasting Room is a nice wine bar with more sofas than tables. Friendly service from the staff and plenty of space for groups wishing to sample various wines and foods. A full menu is available for those wishing to do more than drink.

  • Rockit Bar & Grill $$

    22 W Hubbard St

    The Rockit Bar and Grill sports a dim atmosphere and casual eatery to go with its drinks. You can get foods like BBQ and burgers to go with your beer. The big selling point of this bar is the exceptional customer service from the staff.

  • Rosa's Lounge $$

    3420 W Armitage Ave

    Rosa's is the place to go for a friendly atmosphere and blues music playing in the background. While there is no food and furnishings are basic (and also it's a little out of the way to travel to), expect a crowd when there is a concert.

  • Smart Bar $$

    3730 N Clark St

    Smart Bar is considered the best club from the birthplace of electronic house music. The sound system is unrivaled for music and dancing. While small and not centrally located, it is the sort of place that is sought out rather than found.

  • Neo $$

    2350 N Clark St

    Neo is considered one of the premiere Goth Bars for Chicago. Hard techno music and pale women with such fashion statements as fishnets and mohawks fill the landscape of the club. The bar is still friendly to those that dress mainstream.

  • Brandos $$

    343 S Dearborn St

    Brandos is an old school speakeasy that also has karaoke every day of the week. Cheap drinks and interesting crowd with a good atmosphere and friendly service. Small and dimly lit, this place attracts the more professional crowd of Chicago.

  • Nacional 27 $$$

    325 W Huron St

    Nacional 27 is a Chicago club for the Latin American dancer. A nightclub on the weekend evenings and a restaurant otherwise. The Ceviche washed down with a Caipirinha is a good reason to go. Quiet dining area with an upscale feel to it.

  • Sound Bar $$$

    226 W Ontario St

    The Sound Bar is huge, with multiple floors that can lead to a disorienting atmosphere when it's crowded. Despite the crowd, it's a clean place with a typical club vibe. The main attraction is the Go-Go Dancers that liven up the place.

  • Sub 51 $$$$

    51 W Hubbard St

    Sub 51 (located under Hub 51) always has a beat echoing through its rooms, keeps itself clean, has a friendly staff and serves top-shelf liquor. This club tends to get crowded particularly on the weekends so find your table and stay at it.

  • The Underground $$$

    56 W llinois St

    The Underground is one of the premiere clubs of Chicago. A rotating list of celebrities and famous DJ's can be found here. Other specialities include the top-secret military hideaway theme and drinks like the Bond Girl and Hunters Moon.

  • Cuvee $$$$

    308 W Erie St

    Cuvee nightclub in Chicago brings a hip Vegas and Manhattan atmosphere to the Chicago nightlife scene. Featuring a large dance club floor, dark decor and well known DJ's as well as good music, strong drinks, and beautiful people

  • Detention $$$

    9 W Division St.

    Offers great music every night with sexy staff dressed in provocative school girl uniforms themed around high school detention. Located in Chicago's most legendary party area notorious for its crowded streets & wild late night party venues.

  • The Shrine $$

    2109 S Wabash Ave.

    The Shrine is the real deal for those who bleed hip hop. The crowd is always diverse in every aspect and the club features house music on one side, hip-hop and dancehall on the other end with different musical themes being offered each week.

  • GibsonsSteak and Seafood$$$

    1028 N. Rush St.

    Gibson's serves one of the elite steaks of the city of Chicago. Sharing a kitchen with Hugo's Frog Bar and Fish House, the restaurant has six private rooms that can hold groups of any size. Save room for the martinis and huge desserts.

  • AlineaGourmet Experimental$$$$

    1723 N Halsted St

    Alinea is best known for its gourmet, ultra-modern, experimental approach to dining. It was declared the "Best Restaurant in America" by Gourmet Magazine in 2006. Bring a full wallet as the average dinner is priced at around $210.

  • The Capital GrilleSteak and Seafood$$$$

    633 N. St. Clair St.

    While some might snub a chain like the Capital Grille, their menu is certainly creative enough to warrant a taste. Several signature steaks dishes adorn the menu plus there is quality service and cocktails. Private rooms are available.

  • Girl & The GoatAmerican$$$

    809 W Randolph St

    If you're travelling to Chicago and want to eat at Girl & The Goat, it's best to make reservations as early as possible. This restaurant is known for great food, great service and reasonable prices. Be sure to try the pretzel bread.

  • Charlie Trotter'sAmerican$$$$

    816 W. Armitage

    Charlie Trotter's is considered one of the best restaurants in the world. It has three daily tasting menus: the Grand Menu, the Vegetable Menu and the Kitchen Table Menu. The owner has written 11 cookbooks and hosts his own cooking show.

  • Les NomadesFrench$$$$

    222 E. Ontario St.

    Les Nomades is a French gastronomic adventure. The attentive service is superb and the Wine Line is unmatched. Private dining is available for parties of up to 44 people. It's a sophisticated experience with the ambiance of a private club.

  • 1492 Tapas BarSpanish$$

    42 E. Superior St.

    Experience the many different parts of Spain in a single restaurant. 1492 is located in a Victorian mansion with four levels of dark wood, stained glass windows and a spiral staircase. Extensive Spanish culinary menu at reasonable prices.

  • TruFrench/American$$$$

    676 N. Saint Clair St

    Zagat Survey voted Tru as one of the most popular restaurants in Chicago. Chefs Rick Tramonto and Gale Gand create their culinary art with a theatrical flair. Excellent showmanship make this a house of worship for food-lovers and critics.

  • SixteenAmerican$$$$

    401 N Wabash Ave, 16th Fl

    Located on the 16th floor of the Trump International Hotel and Tower, Sixteen offers fantastic city views to go with its menu. The tasting menu changes daily and makes Sixteen among the most elegant and gorgeous restaurants in the city.

  • Keefer'sSteak and Seafood$$$

    20 West Kinzie St.

    Keefer's offers one of the best steakhouses in Chicago. This carnivore's dreams offers entrees like a 22 oz T-Bone and a 17 oz New York Strip Steak. For those pescetarians, the fish menu is also top-notch and includes sole and lobster.

    There are no music venues in the database
  • Admiral Theater $$$

    3940 W. Lawrence Ave

    Once serving as an adult movie theater, the Admiral Theater has evolved into a live entertainment establishment. The club is fully nude, which means there is no booze. Fortunately, there is a bar two doors down and dances are cheap enough.

  • Pink Monkey $$$

    750 S. Clinton St

    Consisting of impeccable talent and a tight space, the Pink Monkey is very close to the actual city of Chicago. Despite the name, it's most definitely a man's club. It is BYOB, so remember to pack your own beverages on the way to the club.

  • Industrial Strip $$$

    3626 S. Calumet Ave

    Located in the neighboring state of Indiana, Industrial Strip is a scant 20 miles from Chicago proper. Consisting of reasonably priced dances, private rooms and a low-cost ATM, this club sadly does not permit alcohol. Still a fun time.

  • Club 390 $$

    390 E. Joe Orr Rd

    There are only five words necessary to sell this club as a potential party location: full nude and full bar. While over 30 miles away and somewhat seedy, the policy of full friction dances make the trip worth it. Plus Party Rooms!

  • Atlantis Gentlemen’s Club $$$$

    1897 Lincoln Hwy

    As one of the more upscale clubs in this list, it's well worth the twenty minute ride from Chicago. Vegas-style in most ways, it includes Plato's Penthouse high above the main floor. Warning: high prices accompany the huge size and decor.

  • Scores Chicago $$

    4003 W Lake St

    Scores is the name brand of strip clubs with branches all over the world, so you know what you're getting. Quality dancers and atmosphere and your group can text SCORES to 69302 for free passes. Located conveniently near the airport.

  • VIP’s: A Gentlemen’s Club $$$

    1531 N. Kingsbury St

    Good news and bad news here. The good news: VIP's offers a full bar. The bad news: no nudity, instead some sort of latex nipple covers. Still, the talent is good and the drinks are strong (particularly considering the occasional deals).

  • The Skybox Chicago $$

    16700 S. Halsted St

    It's a sports bar! It's a strip club! It's a sports bar and a strip club! With big TV's and high-top tables and stools, this could be the Reese's Peanut Butter Cups of clubs. Worth the trip for the reasonably-priced drinks alone.

  • Heavenly Bodies $$$

    2835 E. Higgins Rd

    Heavenly Bodies won't win any awards for cleanliness or convenience, but it does have a low cover charge and cheap drinks (and free food at times). It even has an all-you-can-eat lunch menu that includes the Double D Boobie Burger.

  • Polekatz Gentlemen’s Club $$

    7337 W. 100th Pl

    With 18,000 square feet of space, Polekatz fancies itself a "Vegas-style" nightclub. It has an excellent VIP area and an assortment of Kittens (their term, not ours) to make the experience worth ir. Warning: they hate teetotalers, so drink.

  • Sidetrack $$

    3349 N Halsted St

    Warm atmosphere, classy decor, friendly staff and good drinks mark this Chicago bar. The huge area insures that you'll always have a place to hide and the good service means they'll always be able to find you with your drinks. Dress nice.

  • Roscoe's $$

    3356 N Halsted St

    Events at Roscoe's (such as Pride Day) always draws big crowds with dancing and fun. At reasonable prices, they serve an excellent array of drinks including a Pink Lemonade pitcher (hint: it's not just lemonade). Food is also available.

  • Berlin $$

    954 W Belmont Ave

    Berlin is a very down-to-earth establishment but it can get a little crazy (keep an eye on your wallet). The stage area is sometimes frequented by dancers getting particularly jiggy. Techno music and drinks specials are also the bar style.

  • Big Chicks $

    5024 N Sheridan Rd

    Music, fun and a friendly atmosphere go along with the attentive bartenders and cute crowd. The crowd itself is surprising diverse and you could run into a variety of peoples. There is continuous dancing and drinks are reasonably priced.

  • Scarlet $$

    3320 N Halsted St

    Scarlet takes its name from the tendency of the gay 1920's society to wear scarlet in their clothing (more details are on the website). Considered one of the best gay bars in Chicago, Scarlet has good service, good drinks and a great crowd.

  • Jackhammer $$

    6406 N Clark St

    Despite the clean and spacious interior, Jackhammer is wild, untamed and unashamed. Ask about their very special downstairs bar called the Hole with its own very special dress code. Popular spot for bachelorette parties, ironically.

  • Hydrate $$

    3458 N Halsted St

    Hydrate is like most of the gay bars in this list: good music, reasonably-priced drinks and fun people. Gets crowded during late nights on the weekend. Mondays has drinks specials and no cover before midnight. Must-go place for Pride.

  • @mosphere $$

    5355 N Clark St

    Besides being a fun bar and club, @mosphere has special events in the early evenings for those wishing for more intellectual pursuits (literary clubs, etc.). For those wishing for more carnal entertainment, they play gay porn on the TVs.

  • Spin Night Club $

    800 W Belmont Ave

    What distinguishes Spin Night Club is the outdoor patio available for patrons of the club. You can watch the drag show in the downstairs portion of the club, a shower show upstairs or just people watch and play pool near the entrance.

  • Cell Block $

    3702 N Halsted St

    Friendly bar staff and fun clientele make Cell Block memorable for the average patron. Reasonably priced drinks also make it a worthwhile trip, plus you can watch Grey's Anatomy and porn run side-by-side on the televisions at the bar.