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Chicago dating guide advises how to pick up American girls and how to hookup with local women in Chicago. Travel, enjoy and have fun with hot single girls and you might even meet the love of your life. Read more on how to date American women, where to find sex and how to get laid in Chicago, Illinois, United States of America.

Chicago skyline

Chicago is officially referred to as the City of Chicago. In Illinois, it is the most populated city. Chicago has an estimated population of 2.7 million, making it rank as the third most populated city in the United States of America. Chicago is an international hub for transportation, telecommunications, technology, industry, commerce, culture and finance. The 58 million international and domestic visitors of the city in 2018 made it rank as the second most visited city in the nation.

Chicago Top 10 Overview:

Chance of picking up girls: 4.35 / 5

Picking up at daytime: 4.3 / 5

Picking up at nighttime: 4.4/ 5

Looks of girls: 4.7 / 5

Attitude of girls: 4.4 / 5

Nightlife in general: 4 / 5

Locals' English level: 5 / 5

Moving around the city: 4.6 / 5

Budget per day: US$60 - $800

Accommodation: US$11 - $630

Girls in Chicago

Hot girls of Chicago at the Underground Club

Chicago girls are attractive, classy, ambitious, goal-oriented, driven and they do know how to show it. Just like the city itself, Chicago girls are timeless and classic. During a conversation or an argument, Chicago girls are never afraid to express themselves and voice out their convictions. And food, they love it loads. Chicago girls do know how to eat, especially pizza or a sloppy Italian beef sandwich. This doesn't mean they are shapeless and fat, in fact, a large number of them are sporty and they are true lover of sports. Girls in Chicago are naturally good-looking, humble and down to earth. However, they do know how to have a good time and they are very funny too. If you're hanging out with a Chicago girl, erase any thought of boredom probability in your mind. If you're not convinced about that, stroll around River North where you'll see lots of gorgeous Chicago ladies having a good time. Girls in Chicago are the Girl-boss type, they know what they want and they are never scared to go after it, they are brave.

RatingLooks Looks of girls: 4.7 / 5

Chicago girls are beautiful and attractive. You will find African American, European American, Latinos and even a fair number of Asian girls in Chicago.

RatingAttitude Attitude of girls: 4.4 / 5

You can never get bored hanging out with a Chicago girl. They are funny, classy, lively and very welcoming. However, only the sophisticated ones can easily attract a Chicago girl.

Where to Get Sex Now

It is easy to get sex online in Chicago. You just need to find the best available girls. See Girls Online Here!

How to Pick Up Girls

RatingPickup Chance of picking up: 4.35 / 5

Without an iota of doubt, Chicago is one of the most beautiful cities in the United States of America that is blessed with unique and beautiful women. Foremost, you must understand that picking up a Chicago girl is easy provided that you can 'talk'. What this means is that, girls in Chicago prefer guys who can approach them and express their intentions and emotions rather than those who throw chat up line at them. The weekend is considered as the best time to pick up girls in Chicago. This is because you won't have much luck during the week for the city tends to ‘sleep early’.

Tips for Daytime

RatingDaytime Chance of picking up at daytime: 4.3 / 5

If you're up for some daytime gaming and you're looking for single women in Chicago walking around, you'll find a lot of them all along Michigan Avenue. If you want to meet professional women in Chicago in the day, Loop business district is where you should be to approach anyone of them that catches your fancy. Especially during lunch or rush hours, you'll find them mostly in bars and cafes. Another tip for daytime gaming is to chat with beautiful Chicago girls online. Although Chicago girls love to be approached physically, one cannot put off the fact that girls generally cannot do without staring at their phones, You can always find beautiful girls in Chicago who are looking for who to have sex with on Adult Friend Finder.

Michigan Avenue

Best Places to Meet Girls

There are lots of places where you can meet girls of different sizes and personalities in Chicago. Generally, it is not hard to meet girls in Chicago, you just have to go outside, explore, be yourself and put on your best version.

Shopping districts and malls are one of the best places where you can meet girls in Chicago. Here is list of top shopping districts and malls in Chicago where you can meet different girls:

  • Woodfield Mall
Woodfield Mall
  • Fashion Outlets of Chicago
  • Harlem Irving Plaza
Harlem Irving Plaza
  • Chicago Premium Outlets
  • Westfield Old Orchard
Westfield Old Orchard
  • Water Tower Place
Water Tower Place
  • Chicago Ridge Mall
Chicago Ridge Mall

You can also meet with beautiful university girls in Chicago in the day at the campuses of Northwestern, Loyola, University of Chicago, DePaul and University of Illinois. There is a high population of females in these universities which make it very easy to get hooked up, you just need to be smart and look nice.

Innjoy is another place where you can meet beautiful girls in Chicago. Innjoy sure offers double fun with its two locations, one in Logan Square and the other in Wicker Park. The entertainment venue and casual dining is available all the days of the week: Saturday 11 a.m. to 3 a.m, Sunday 11 a.m. to 2 a.m., and Mon to Fri 5 p.m. to 2 a.m. Innjoy is one of the cool spots where visitors and locals in Chicago love to hangout. Innjoy is at 2051 W Division St Chicago, IL 60622.

Tips for Nighttime

Chicago is a pretty great place to hook up or get laid in general. The girls are welcoming and friendly. All you need to do is to be polite, dress well and charm them by buying them a few drins, complimenting them and you will be good to go.

RatingNighttime Chance of hooking up at nighttime: 4.4 / 5

Magnificent Mile along Michigan Avenue and around Rush Street are the main areas for singles nightlife in Chicago. If you're keen on hooking up with a beautiful girl in the city, it is important that you stay close to the best party hot spot. If you're looking for a one night stand, Magnificent Mile and Well Rush Street have a good nightlife and they are your surest options. You will not only find singles bars and the best nightclubs to pick up hot chicks here but you will also get to see many cool spots for a night date. If you can get a hotel near these nightlife districts, you'll definitely have no regret. Another bar district that has lots of places to sip a beer and attempt getting laid is Wrigleyville. Wicker Park and Lincoln Park also have numerous bars where you can likely hook up with a Chicago girl if you're looking for who to have sex with.

Lincoln Park

One of the best places to pick up girls in the nighttime in Chicago is ‘Tzar’. The venue is a center of attraction to European women in Chicago and a large number of them speak English. Around this club, there are numerous quiet places where you can have an interesting chat with a Chicago woman with a pretty decent music buzzing from the club. Just like other places in Chicago, you are requested to dress sophisticated before you'll be permitted to gain entrance to the venue. Tzar is at 215 W Ontario St. Crescendo is another bar that has a vibe similar to that of Tzar's. It is very easy to gain entrance to Crescendo but it is recommended to visit Tzar if you are truly up for picking up a beautiful girl in Chicago.

If you want to pick up a beautiful girl in Chicago who loves dancing, Soundbar at 226 W. Ontairio St is where you should be. The venue has a very good nightlife and the music at this venue is not too loud which makes it very easy to converse with a girl there. Nevertheless, you must get there early if you don't want to stay too long queuing to get in, and if you're not able to get in, you may consider Spy, which is just across the street and has shorter wait times.

If you want to pick up one of the hottest girls in Chicago, Level Nightclub is the destination you should head to. Picking up starts very late in the night and the girls that patronize this venue are SUPER hot! There is no entrance fee but it is important that you arrive early. If you want to experience an awesome night with beautiful Chicago girls, you should go to this club on Sundays.

The Bull and Bear is also another venue where you can pick up one of the hottest girls in Chicago. Although the bar is a bit smaller than Level Nightclub, the women who frequent this bar are fantastically hot. A lot of them will be ready to chat with you and if you do not mind at all, picking up and getting laid is imminent.

Best Nightclubs to Meet Girls

There are lots of nightclubs and singles bars to pick up girls in Chicago. This is a few of the best nightclubs and singles bars to pick up Chicago girls:

  • Kingston Mines
  • Buddy Guy’s Legends
  • House of Blues
  • Stereo Nightclub
  • Nacional 27
  • Smartbar
  • Debonair Social Club
  • HighLine
  • Luxbar
  • Frontier
  • Big City Tap
  • Old Town Pour House
RatingLooks Nightlife in general: 4 / 5

Chicago nightlife is something to witness. The night is always young, the girls horny and the atmosphere eclectic.

Chicago River at Night

Mature Ladies and Cougars

Hooking up with mature women in Chicago is not in any form arduous as long as you know the right spots to be to meet with beautiful cougars in Chicago. If you desire to meet, hook up and probably get laid with an older woman in Chicago, here is a list of favorite spots and cougars bars where cougars in Chicago love to hang out:

  • Howl at the Moon: This one of the best and famous cougars bars in Chicago. Every night each week on a Thursday at the Howl at the Moon, the bar organizes a Cougar night where you'll meet a lot of mature women in Chicago craving for younger men who are in their twenties.
  • The Wild Hare: Fondly referred to as Chicago Cougar bar, the Wild Hare is a relaxed bar where cougars in Chicago visit constantly to listen to some live music and sip on rum every week. You can impress the mature ladies with some super moves on the dance floor or you may just sit at one of the private corners to gaze at the older beauties.
  • Dance Classes: One of the best ways to meet Cougars in Chicago is through dance classes. These mature ladies have interest in dancing because they believe it helps them keep fit and they also get to meet new people. Dance classes would work out well for you if you prefer a more low key setting to seeking for an older woman in a noisy club or bar. Here, you'll get closer, have a direct conversation and you can easily wow her with your amazing dance moves.
  • Parks: If you love hunting for cougars in the day, the local park is a great place where you'll meet and pick up a beautiful Chicago Cougar. In the day, take a pleasant stroll to spots such as Lincoln Park, Grant Park and the Millennium Park, where you'll definitely meet a lot of beautiful cougars who are getting soaked up in the sun, reading a book or stretching their legs.
  • Restaurants: One of the great places where you can pick up a beautiful mature lady in Chicago is at a restaurant. Visit a classy, all-American restaurant where you'll find it easy to see a cougar dining alone with a book or sipping a cocktail at the bar.
  • Sports Clubs: Another fantastic way to meet Cougars in Chicago is taking up a social sport. Social sport, squash or playing tennis is an interesting way to get hooked up with an older lady in Chicago. Improve your fitness and impress her more with your skills. You may try out Lakeshore Sport & Fitness Lincoln Park or Chicago Sport & Social Club and it's likely that you get fortunate to get what your heart seeks.


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Top Dating Tips

While on a date with a Chicago local girl, you can't avoid having a conversation that centers around sport. Make sure you don't mess up by showing a strong support for a team which she is not a fan of, especially if she's a hardcore fan. If you're going on a wine and dine date with a Chicago girl, here is a list of romantic cocktail bars and restaurants you can take her to:

  • Bavette’s Bar & Boeuf
  • Sapori Trattoria
  • NoMi Kitchen
  • Cherry Circle Room
  • Geja’s Cafe
  • Three Dots and a Dash
  • The Violet Hour
  • The Green Mill
  • Billy Sunday
  • Lost Lake
  • CH Distillery and Cocktail Bar

If you're up for some comedy after wining and dining, here is a list of comedy clubs you can go to:

  • Zanies
  • The Comedy Bar
  • Comedy Clubhouse
  • Laugh Factory

If you want to watch a show, visit any of these:

  • The Chicago Theater
The Chicago Theater
  • Broadway Playhouse
  • Goodman Theatre
Goodman Theatre
  • Cadillac Palace
Cadillac Palace

If you are going on an outdoor date, take advantage of the good weather and beautiful summer of the city and take her to any of these places to have a nice time together:

  • Maggie Daley Park
Maggie Daley Park is a re-landscaped section on northern Grant Park in Chicago
  • Lincoln Park
Lincoln Park
  • Garfield Park Conservatory
Garfield Park Conservatory
  • Millennium Park
  • Botanic Garden
Botanic Garden

If you're going on a date during the day with a sophisticated Chicago lady, try out any of these landmarks or museums:

  • Museum of Science and Industry
Museum of Science and Industry
  • Art Institute of Chicago
Art Institute of Chicago
  • Willis Tower (former Sears Tower)
Willis Tower
  • Cloud Gate (The Bean)

Relationships and Love

Thousands of single women in Chicago are searching for a partner and potential future husband. Check out an ultimate guide for dating local girls, relationships, love and marriage: Relationship & Love Guide to Chicago

Online Dating

There are more than 35% of Chicago’s 3 million singles signed up on online dating sites and apps. Here is a list of dating apps in Chicago that are reported to have had the best success:

  • Cougar Life: There are lots of single guys below 35 and attractive older women in Chicago. Signing up for a free trial on Cougar Life is a good way to commence enjoying getting hooked up with beautiful Cougars in Chicago. The app is originally dedicated to men looking for single older women who are 30+ and older women looking for both younger and older men.
  • Elite Singles: If you're looking for a partner who values education, Elite Singles has made it all easy for you. Those signed up on the dating app are those who have completed their diplomas and degrees, the dating app is where you can get connected and hooked up with a professional woman in Chicago.
  • EHarmony: You would totally agree that there are lots of challenges in dating as a single parent especially in a big city like Chicago. The good news is, dating a single parent has been made very easy with eHarmony. With over 15 million members, you can find your compatible single parent and kick-start your fresh love journey.
  • Tinder: When it comes to finding a quick fling, virtually everyone sees Tinder as a last resort. Guys who want to meet with beautiful girls in Chicago on this app must be very attractive or else they will have a very tough time getting hooked up with a girl because there are lots of girls that are getting spammed non-stop. Make sure you upload a very cute and nice photo of yours that will help you stand out from others.
  • Adult Friend Finder: If you're looking for who to have a quick sex with, the first app you should try out is Adult Friend Finder. The dating app has a huge number of users with about more than 50 million members and has a very good attention in the beautiful big city of Chicago.

Live Cam Dating

Are you looking for virtual satisfaction in Chicago? Chat with live web camera models and find the best girl for your needs. There are thousands of girls online 24/7 waiting for you: Live Cam Girls

What Kind of Guys Have the Best Chances

Girls in Chicago do not demand too much from a guy like other girls from other cities. They are classy women in a sophisticated city and to hang out with them, you must be of course sophisticated too.

Risks while Gaming

Although the beautiful city of Chicago is known for being richly sophisticated, the rate of violence in the city is very alarming. Either you're day gaming or out in the night to get laid with a beautiful girl, you must be woke and conscious of all happenings around you.

How to Get Laid as Soon as Possible

A quick way to get laid is to sign up on Adult Friend Finder. Most Chicago ladies looking for who to have sex with sign up on this dating site. Nevertheless, you should also note that some hookers in Chicago take advantage of this online site to get customers.

Gold Diggers and Sugar Babies

Chicago is full of hot girls looking for a mutually beneficial hookup with travellers. There are lots of girls who don’t charge by the hour but who will do anything for a guy who is willing to help them pay their bills. If you are looking for a more personal and less transactional alternative to escorts, a good place to find these sexy open-minded girls in Chicago is SecretBenefits.


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Swinger Clubs and Naturism

There are plenty of swinger clubs in Chicago like:

  • Holiday Club
  • Club Escape
  • Spin

These are also known as lifestyle clubs

Nudity is Illegal in Chicago so no nudist beaches.

Costs of Living

CostsDay Single traveler’s budget per day: US$60 - $800

If you're on a budget trip to Chicago, about $60 to $800 should suffice for a day but this depends on what you plan to purchase or your kind of lifestyle.

CostsAccommodation Accommodation per night: US$11 - $630

Accommodation in Chicago is not so pricey unlike other cities in the United States of America. It can cost you anywhere from $11-$630.

CostsBeerBottle Beer in a grocery shop: US$1 - $3

Beer in a grocery shop will be for $1-#.

CostsBeerBar Beer in a bar or restaurant: US$4 - $8

Beer in a bar or a restaurant will be for around $4-$8.

CostsMeal Meal in a restaurant: US$6 - $70

Meals can cost anywhere from $6-$7- depending on where you eat and what you eat.


Chicago has some amazing accommodations and the best part is that there is something to cater to everyone's budget. Cheapest accommodation is for around $11 where as 3-5 star hotel will cost you from $45-$630.

Trump International Hotel and Tower, Chicago, Illinois

How to Get There and Move Around

By air: There are two major airports in Chicago, they are: O'Hare International Airport and Midway Airport.

O'Hare International Airport: The airport serves numerous domestic and international carriers. It is 17 miles (27km) northwest of downtown. The airlines with the largest presence is the United Airlines with about 50% and closely followed by American Airlines with about 40%. KLM, Iberia, Lufthansa and British Airways are the transatlantic carriers. O'Hare serves flight that connect smaller cities in the Midwest and it is one of the busiest airports worldwide, known for its cancellations and delays.

O'Hare International Airport

Midway International Airport: It is the largest airport for Southwest Airlines as it is 10 miles (16km) southwest of downtown. The airport serves majorly low-cost carriers. Midway is quite closer to downtown and it's a considerable choice because it's often cheaper, less crowded and has just few delays. Airlines serving Midway include Volaris, Sun Country, Southwest, Porter and Delta.

Midway International Airport

Milwaukee 's General Mitchell International Airport: This is another minor airport in Chicago. It is served by 7 Amtrak trains every day except on Sunday when it is served by 6. It takes about one hour and 15 minutes to get to this airport from Chicago Union Station.

By bus: Burlington Trailways: It serves several daily buses heading to Omaha, Des Monies, Iowa City and Davenport at prices that are competitive.

Greyhound: The principal terminal is close to the southwestern corner of the Loop and secondary terminals are at the Cumberland blue line station and the 95th/Dan Ryan red line station. It offers regular service to destinations throughout the Midwest connecting Mexico, Canada and most of the United States of America.

Indian Trails: It offers day-to-day motorcoach service throughout the lower and upper peninsulas in Michigan and it runs one of the largest fleets of deluxe motor coaches. Its services include casino runs, airport transfers, shuttles, tours, bus charters and daily scheduled routes into Duluth and Chicago including Milwaukee and throughout Michigan. It offers express bus service to/from Toledo, St Paul, St. Louis, Nashville, State College, Omaha, New York, Minneapolis, Milwaukee, Memphis, Madison, Louisville, Little Rock, Kansas City, Iowa City, Indianapolis, Grand Rapids, Detroit, Des Moines, Dallas, Columbus, Columbia, Cleveland, Cincinnati, Chattanooga, Atlanta and Ann Arbor.

Peoria Charter Coach Company: It offers day-to-day service between numerous cities and universities/colleges around the Illinois area. Chicago, Champaign, Normal, and Peoria are its common destination.

Wisconsin Coach: It offers 14 buses every day, leaving each bout from O'Hare to Milwaukee and Southeastern Wisconsin as well as Milwaukee Airport.

By car: People in Chicago prefer to identity most of their expressways by their names and not by the usual number. The Stevenson Expressway, Bishop Ford Freeway, Chicago Skyway, Dan Ryan south of downtown, The Kennedy north of downtown and the Edens Expressway are the major expressways that connect the city. Taxis can also get really expensive but a great option for travelling short distances. Uber or Lyft is and alternative option.

Taxi in Chicago

By train: In the whole United States of America, historically, Chicago is the rail hub and one of the most convenient cities to visit by train.

Train in Chicago

By boat: Sea is not a major means of transportation in Chicago but if you want to get a boat cruise, you can get on it!

Navy Pier

Visas: Getting to Chicago requires an application for Electronic System for Travel Authorization (ESTA) or a U.S. visa. The ESTA is not available for everyone but only for citizens of thirty-eight countries in the Visa Waiver Program. The ESTA allows travelers to visit the United States of America for medical purposes, transit, business and tourism for up to 90 days. Travelers who are not eligible for an ESTA can consider a visa application to Chicago which will take more time.

Digital Nomads and Remote Work

Finding remote works in the city is easy, you just have to check up on some websites online.

Internet and Mobile Operators

These are the best internet providers in Chicago are:

  • AT&T
  • Xfinity
  • Spectrum
  • RCN
  • Viasat
  • WOW!
  • Atlantic Broadband

There is a Public WiFi at these Spots in Chicago:

  • Chicago O'Hare International Airport
  • Midway International Airport
  • Millennium Park
  • The Art Institute of Chicago
  • Chicago Public Libraries
  • Museum of Science and Industry United Center
  • The Peninsula
  • The Field Museum
  • Museum of Contemporary Art
  • The Cultural Center
  • Virgin Hotel Chicago

Gambling and Casinos

Top Casinos in Chicago:

  • Rivers Casino
  • Ameristar Casino Hotel East Chicago
Ameristar Casino Hotel East Chicago
  • Horseshoe Hammond Casinos
  • Big Top 2
  • Atlantis Paradise Island Bahamas
  • Majestic Star Casino & Hotel
  • Kiki’s Gaming Lounge
  • May’s Lounge
  • Olivia’s Place
  • Golden Dragon Casino Shuttle Tours
  • Win Star Casino Boat
Win Star Casino Boat

Weed and Drugs

In the State of Illinois generally, it is illegal to possess any amount of Marijuana. Marijuana is legal for medical use in Chicago and you can purchase Medical Marijuana only from accredited Medical Marijuana Dispensary in the state with a Medical Marijuana card. Nevertheless, the procured Medical Marijuana is for personal use only and must not be used in public.

Health, Fitness, Gyms and Massage

Top Gym centers in Chicago:

  • Bucktown Athletic Club
  • Anytime Fitness
  • Wicker Park Fitness
  • Urban Athlete
  • Lakeview Athletic Club

The Best Places for Massage in Chicago:

  • Massage Envy
  • Fit Foot
  • Allyu Spa
  • Mario Tricoci Hair Salon & Day Spa
  • Spa Space

STDs and HIV

In 2017, 19,704 people were living with HIV in Chicago. Of the total figure, 22.0% were White, 20.9% were Hispanic/Latinx and the race with the highest rate of 51.0% was Black. In the same 2017, 81.2% of male and 18.8% of female were living with HIV. According to the Chicago Department of Public Health (CDPH) HIV/STI Surveillance Report, Congenital Syphilis, Syphilis, Gonorrhea and Chlamydia are the common Sexually Transmitted Diseases (STDs) in Chicago.

Stay Safe

Despite a big decline in the crime rate from the 1970s and 1980s, Chicago is still a big city with big city problems. There are run-down areas within a few blocks of some well-traveled places such as near the United Center and Guaranteed Rate Field. The majority of the city's violent crimes occur within a relatively small number of deeply impoverished neighborhoods well off the beaten path in the South and West Sides, but given the chance nature of crime, you should exercise the usual precautions wherever you go. Even in a neighborhood with a bad reputation, though, you might still have a perfectly good time, as long as it falls within your comfort level.

See Also