Your After Dark “Bucket List” for visiting Chicago on a “shoestring budget”

An After Dark Bucket List for Chicago on a “shoestring budget


Let’s face it, vacationing in big cities is a challenge, and we are always trying to find ways to “stretch” the old wallet, aren’t we?

That being said, this shouldn’t keep us from doing just that! What I mean is, we need to take vacations and visit new places, and still be able to keep spending in check.
This article is my attempt to show you how to accomplish just that, in the “Windy City”, Chicago, Illinois, U.S.A.

There’s plenty to do in Chicago during the day when this city is alive with people, from parks, museums, waterfront activities and much more. However, it’s after hours that this old city really comes alive. Remember, this is where the old time mobsters ran backroom joints or “speakeasies” that packed at night to the music and cheap illegal booze.


Famous Chicago Skyline

The first thing besides travel plans to Chicago that must be addressed is where you will be staying while here, and keeping on your budget. One suggestion for you, if you’re looking to experience Chicago’s “shady” past while staying in a piece of history would be the Congress Hotel. The rumors have it that Al Capone, the infamous gangster from days of Prohibition, lived and possibly owned this hotel.
They also say his ghost can be heard walking it’s halls at night, his wingtip shoes tapping on the tiles.

Money Savings Tip: Secure your best hotel rates in Chicago during Fall/Winter months at

While keeping on the “shoestring” theme, why not start out your evening with special happy hour deals, where discounts and sometimes “free” is the word?

Many bar/restaurants offer special discounted prices on food and drinks between 4PM and 6PM, just perfect to fill up before heading out on the town. We hope you find this list of a few helpful during your visit.

The Florentine Between 4-6 PM, order a drink from the bar and you get a
151 W Adams St. free pizza!

Hub 51 Who doesn’t love sushi? Who doesn’t like the expense of
51 W Hubbard St eating sushi? Show up between 3-6 PM or 11PM until
closing time and all sushi is half price.

Bull & Bear This open and airy sports bar has an excellent appetizer
431 N Wells menu that’s half price from 3-7PM weekdays.


Happy Hour can be a cheap & fun dining alternative

During the day Chicago streets are bustling with active busy bees, crowded beyond belief to many visitors. When the sun goes down it’s a whole different city, and you as a visitor can see the sights most people don’t.

The downtown Chicago lights against the night sky is a thing of beauty. Why not head to Millennium Park and enjoy taking a stroll around the Crown Fountain and Cloud Gate, known as “The Bean”, a massive golden sculpture. Experience the city in all its twinkling beauty, and don’t forget that camera.

For an evening of dancing, entertainment and possibly a light late night “snack” here’s a popular option. There’s no place for a pub-crawl quite like the Rush and Davidson Streets in the Gold Coast neighborhood. Head to the ever-popular Hangge-Uppe, a quirky 2 level bar with three dance floors, open till the wee hours. You can play shuffleboard at Mahoney’s Pub or Ping-Pong at Streeters. Depending on the hour and how hungry you are, right next door is a great hot dog joint to sample a traditional Chicago-style dog.


There’s only one “Chicago-Style Hot Dog”!

Another excellent and totally fun experience for adults, singles or couples is the ever-popular “Adler After Dark”. This is an event held at the Adler Planetarium offering you unlimited access to shows and other unique entertainment. This experience, which is exclusively for adults 21 or over, changes every month making it unique and exciting. Enjoy multiple bars, music and one of the very best views of the Chicago skyline. As you plan your visit to Chicago, you might want to contact the Adler Planetarium to find out more, and if it’s happening during your stay. Keep in mind, advanced tickets will run you only $15 per person, and well worth it.

And then there’s Chicago Jazz! Long known for their Jazz clubs and after hour’s clubs, there’s no shortage that you might want to visit at night. Our thought is to recommend one of the best-known clubs, Andy’s Chicago Jazz as an experience that you can enjoy for hours and it won’t break the bank, if you don’t let it. Keep in mind that getting a table might take some time and patience, but it’s well worth it.
Andy’s offers you casual dining options along with music by Chicago’s top Jazz artists. Most nights the cover charge is only $10, and if you stick to appetizers or pizza with that beer, it’s a cheap evening.

Money Saving Transportation Tips:

1. Forget the rental vehicle.
Why complicate life and especially your vacation getting lost, trying to find a
parking space or paying for parking garage space, and spending all that money
on a rental anyway? And don’t forget extra heavy traffic in the city.

2. Get an “L” Train and or Metra Rail map and schedule, and use what
Chicago uses to get around the city. The “L” Train one-day pass is $10 and three-
Day passes are only $20.
If you are heading into the suburbs, take the Metra Rail for between $2.75-$9.00
one-way depending on how far you’re going. The nice thing is on weekends you
can score a weekend pass with un-limited travel for only $7.00.

3. Take a Taxi or Water Taxi to get from point A to point B. Sometimes this is the
best way to travel, especially to dinner. If you want to impress your date, taking
a Water Taxi to the Loop or China Town could be the right ticket. There are two
companies offering this service, Chicago Water Taxi and Shoreline Sightseeing,
both offering day passes.

About storiesbygary

I am a Freelance Writer / Photographer, writing travel related articles for international magazines, blogs and websites and my own published books.
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