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Meeting Girls in Chicago: Is it Worth it?

by The Masculine Traveler
Chicago USA datasheet and dating guide

Meeting girls in Chicago, was much better than I had expected. With a population of almost 3 million, the Windy City is the 3rd largest city in the U.S. Chicago is often referred to as “New York done right”. The moderate costs, cleanliness and Midwestern charm give credence to this sentiment. The following will highlight the best places to meet girls in Chicago.


The Masculine Traveler Rating Guide

Attractiveness of local women: 3/5
Receptiveness to Daygame approach: 4.5/5
Receptiveness to Nightgame approach: 3.5/5
Logistics: 4/5
Cost: 3.5/5
English Levels: 5/5



The famous Chicago winters are frigid and snowy, while summers tend to be hot and humid. I find the spring the best time to visit.



The city feels segregated, but has an even distribution of ethnicities consisting of roughly: 1/3 White, 1/3 Hispanic and 1/3 Black. You will notice a lot less Asians in Chicago as compared with New York.



Chicago is a first rate city with moderate costs. Food and booze are priced fairly. My friend pays under $1000 per month to live in Lincoln Park. However, Downtown hotels are not cheap, starting at $100 per night.



O’Hara International Airport and Midway Airport (more like a bus station) are the two main airports.

I usually use Southwest points to fly in to Chicago. You can book Chicago one-way from Major American cities for as little as 5k points.

Soutwest points are a great way for domestic travel.

There are plenty of taxis. Expect to pay $40-$45 from O’Hara to Downtown and $30-$35 from Midway. Uber is a good option and slightly cheaper.

Downtown is very walkable. The streets are clean, wide and have little congestion, outside very touristy areas.

Chicagoans have a strong sense of pride about their neighborhoods. Neighborhoods consist of Downtown, Northside, Southside and Westside.

The Loop is the main financial and cultural of the city, located in Downtown. River North by the Magnificent Mile  is the best location set up shop, particularly on a short trip. You will have plenty of bars, restaurants and Daygame options within walking distance.

I love the logistics and have stayed at some cool hotels in the by the Magnificent Mile. You will have no problem bringing girls back to you hotel.

The following were all hotels that I have stayed at and recommend for logistics and a quality stay:

Doubletree by Hilton Chicago

Kinzie Hotel

Inn of Chicago


Lakeview/Lincoln Park are upscale neighborhoods with a slightly suburban feel. There are plenty of cute chicks roaming around. There are less hotel options than the Loop, so looking into Airbnb is your nest option for accommodations.





Tourist Attractions

Magnificent Mile

Chicago USA Datasheet and Dating Guide

The Bean
Sears Tower
John Hancock Building
The Art Institute of Chicago



Jokingly, I refer to Chicago with my friends as “the land of the 6.5s”. Girls won’t blow you away with their looks and style. However, two qualities struck me about the women.

1) Approachability, women almost always stop when doing a direct approach on the street. It is clear that they are not getting approach often. This is one of the most receptive cities I have visited for Daygame.

2) What they lack in stunning beauty, the girls here more than make up for in personality. Girls are genuinely sweet and display Midwestern hospitality.

Chicago USA Datasheet and Dating Guide


Online Game

You should have the same expectations in Chicago like any other American city. Cracking above the 8 range will be difficult unless you have superb looks/pictures. There are plenty of girls in the 6 range that you can target through online. Higher quality will require good old fashion approaching.

For online, I recommend OKCupid and Tinder.



As previously discussed, Daygame is the way to go. Women are receptive and approachable during the day. The biggest problem is that it is too cold to do street approaches for half the year, due to the weather. Fortunately, Chicago has some large malls and plenty of cafes and coffee shops to take care of business during the day.



I stuck mostly to Daygame but I have partied at night. For you night owls, there are some solid options in Chicago ranging from the typical Irish pub to upscale clubs. I enjoyed bar hopping in Wicker Park and was satisfied with the talent. I also suggest hitting up some of the neighborhood bars in Lincoln Park, particularly if you are set up with an apartment on the Northside.



I have been to Chicago a few times now. I plan to head out there 1-2x per year to hang out with friends and run some Daygame. Chicago is my favorite American city and one of the best Daygame places you will come across. The girls won’t blow you away with their looks, but there are a plethora of cute, sweet and approachable girls.  I was able to pull a solid 8 early 20s brunette to my hotel from an approach at a mall.  I didn’t get the Bang that night but closed shortly after that day.

Read more on Dating In New York




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