TG Guide to the Chicago Area

Clarification: The primary author of this page (Annie) does not live in the Chicago area, but has visited frequently ever since she was a child.

This is a report based mainly upon the history of Pinkfest. It's not a guarantee. Do {whatever} at your own risk. If something breaks, you own all of the pieces. :)

This information is hearsay. It contains pointers to places people have been, things people have done, and shops people have used and reported good things.

Nothing is without risk! Use care and common sense, remain street-wise, and consider time, place, and circumstance when doing anything.

Don't push things, remember, you're in Chicago to have a good time, not to change the world.

The people for whom this guide is intended are either those who wish to blend well in mainstream venues, or those who wish to go to places that are known to be accepting of those who are transgendered.

Some of the emphasis is toward people who are new to public exposure in general, and those who are new to visiting Chicago.

The topic of where to go to meet potential partners, casual, long-term, or professional, of any gender or any persuasion, is not covered.

Chicago, the Windy City, is a TG-friendly city for the most part. Both the local residents and the other visitors display a very strong live and let live attitude for the most part. It is, however, hardcore big-city, mainstream America.

Very few problems and essentially zero hostility have been observed in the Chicago area since Pinkfest began in 2001.

Strong Suggestions:

Remember, Chicago is a mainstream general-public envronment. This means mainstream dress and mainstream behavior!

  • Don't overdress! Dress in a manner similar to other women of your age, height, size, and fitness level. Be sure your outfit is appropriate to the time, place, and circumstance of your activity.
  • Don't hang around in groups! Yes, this is one of the hardest suggestions to follow, but groups of TG's do attract attention -- a lot of attention.
  • Wear comfortable shoes! Unless you have your own private chauffeur, you will be walking a lot and spending lots of time on your feet.

Dress, style, behavior:

Don't overdress! You want to blend in, not stand out!

For Chicago visitors and tourists, casual dress is the uniform of the day. Casual to dressy is seen in the evenings, but casual still seems to predominate.

If you're new to Chicago, first observe the dress and behavior of the gg's who are of your approximate age, height, body type, and fitness level. Use them as a model for your mode of dress and comportment.

If you're just dying to wear something more exotic in public, yes, there are places where it's appropriate. See the Big List. (link below)

In general, the main downtown "Loop" area, the River North entertainment district, and the Lakeview ("Boystown") area have been observed to be safe for those who are transgendered, day or night.

Likewise, the popular tourist attractions, such as Navy Pier, the Museum Campus, the Museum of Science and Industry, Grant Park, Hancock Building, etc., will be quite safe. (Remember: Mainstream dress and mainstream behavior.)

The "Loop" area, named after the circuitous El tracks in the area, comprises the central business district with the theater district in the north Loop area and shopping, dining, and hotels throughout. The "Museum Campus", with the Field Museum of Natural History, Aquarium, Planetarium, etc., is just to the southeast of the Loop, south of Grant Park.

The River North Entertainment District is just north of the Chicago River, from Navy Pier at Lake Michigan, westward to Franklin St. or so, intersecting the Magnificent Mile shopping district.

River North contains countless restaurants, bars, shops, tourist attractions and such.

The Lakeview district spreads north and west from the Belmont, Clark, Halsted, and Broadway area. This is Chicago's main concentration of "Alternative" bars and clubs. The area contains countless small shops and restaurants as well.

Where to stay:

As for accommodations there are basically two choices, the downtown and central areas for $100 plus per night, or in the outlying areas for considerably less.

In the River North area both the Best Western River North (Ohio at LaSalle) and the Red Roof Inn (Ontario at St. Clair) are decent modest places which are priced somewhat lower than most in the area but still comfortable. The BW River North offers free guest parking, which is the exception to the rule for hotels in this area.

Most of the major hotel chains are represented in the vicinity of both the Midway and O'hare airports at much more reasonable prices. There's also a bolus of very reasonable places in the vicinity of the Halsted and I-80 interchange. (waaaaay south) All of these will offer free guest parking.

Getting around:

The good news is that the Chicago area streets are laid out in a somewhat sane and easy to navigate grid pattern.

The bad news is that this grid does have gaps and holes, streets can change names in the middle of a block, and many streets and expressways can be very congested. Many streets are not marked or maintained as well as in smaller communities. Rough spots and potholes abound!


It's an understatement to say that driving in Chicago can be a challenge.

If you're not used to driving on congested city streets and on busy urban and suburban expressways, you might want to consider an alternate mode of transportation.

Rental cars are available at both airports in the $25-30-ish range per day, not including additional insurance, which you might wanna consider!

What to do with that car when you're not actually driving it is another thing. See parking below.

Public transit:

Both the CTA bus lines and the El/subway system are considered to be safe for those who are TG as long as you don't overdress, don't board in large groups, and behave appropriately.

Taking the "El"

The Chicago El system is one of the fastest and most convenient ways to get from point A to point B in the Chicago area.

No incidents have occurred regarding the El system within the history of Pinkfest.

Of particular interest are the frequently-made trips, such as:

  • Midway and O'hare airports to the downtown and River North area.
  • Downtown and River North to the Lakeview (Boystown) area.
  • Downtown and River North to some of the popular destinations in the west suburbs.

You purchase a fare card via vending machine at the entrance to any El or subway station. You select how much money appears on your card, from the minimum fare upward. You may also add value to your card at the same machine.

Special unlimited Visitor Passes are available at the airports and at various other locations throughout the area.

When you enter the turnstile, you "dip" your card into the card reader. The fare is debited from your card and your card is returned to you just before the turnstile unlocks.

When boarding a train, the correct etiquette is to quickly take any available seat. Some of the longitudinal seats are marked "Priority Seating" and are reserved for seniors and those with disabilities.


In downtown Chicago and the immediate surrounding areas, free parking is a rare exception. Parking will almost always be available and reasonably convenient, but it will be expensive!

If your hotel does not provide free parking, plan on at least $25 per day for parking. Be aware that not all garages used by hotels offer in-out driving privileges without paying another ransom. Many garages are not open 24x7.

On-street parking is available but scarce in the River North and Lakeview areas. Expired meters are strictly enforced! The residential neighborhoods in the Lakeview area have "Zone Parking" reserved for residents only.

Many shops and restaurants offer valet and discount parking in nearby lots. Use it, don't abuse it, as most all of these have time limits and attendants are always looking out for those who go elsewhere after visiting the sponsoring business.


Yes, you will be! :)

Where to shop:

The "Magnificent Mile" along Michigan Avenue is considered to be the world's shopping capital. You can literally spend days in this area without visiting it all.

Water Tower Place (Michigan between Pearson and Chicago Av.) is a multi-story indoor mall anchored by Marshall Fields.

Nordstroms (Michigan and Grand) has an adjoining mult-story mall of smaller shops.

Hundreds of shops appear along Michigan Avenue in this area.

"Mag Mile" shops do tend to be spendy! For those on a budget, here are a few offering some bargains:

Of particular interest to the community are Transformations By Rori and Janna's Place. See the Big List for information.

Where to eat:

We have yet to see a Chicago area eatery that does not appear to want TG business!

Everything from fast food to three-figure-per-person dinners will be available in the River North area. You'll see every major chain (Hard Rock, Rainforest, Lawry's, Hooters, Benihana, Ruth's Chris, ESPN Zone, California Pizza Kitchen, etc.); popular local places such as the original Pizzaria Uno, under separate management from the chain, and its sister, Pizzaria Due, Portillo's/Barnelli's, Billy Goat's ("cheeseborger, cheeseborger, no Coke, Pepsi"), Carson's, Ed Debevic's; as well as countless little holes in the wall, coffee shops, breakfast hideaways, etc.

Some favorites:

Bars and night life:

We've been to several of the Lakeview (Boystown) area bars but have barely scratched the surface. There are countless places along Belmont, Clark, Halsted, and Broadway. There's a bar for every taste. With very rare exception, all bars and clubs in this area will welcome your business.

A few other faves in other areas:

Where to avoid:

General rule of thumb is that if you don't know where you're going in the Chicago area, then don't go there!

Chicago, like any other metropolitan area, has its share of high-crime and unsafe areas. Also, like other cities, the neighborhood can change from perfectly safe to downright scary within a few blocks.

The "rougher" areas of town tend to be to the south, southwest, and immediately west of the downtown district, although there are some questionable areas just to the west and northwest of the River North area as well. (Yes, yes, I know that a lot of very good people live and work in these areas. These are the areas that have higher crime rates, plus there's not really anything of interest to the TG community in these areas.)

To see the Big List of suggested places to go, click HERE