Top Five Things to Do in Chicago This Weekend

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Things get interesting in Chicago on the weekend.  You can see the change from the City That Works (Chicago’s motto) to the City that knows how to relax and have fun.

There are so many things to see and do in Chicago.  But you can carve out a good time in the Windy City if you only have a weekend.

In this article, I will be discussing the following:

  • top five things to do in Chicago during a weekend stay
  • the best place to stay in the Chicago downtown area
  • tips and recommendation to ensure you have a great time


Best place to stay in Chicago downtown

The best place to stay in Chicago downtown is theWit Chicago (for real that’s how it’s spelled).  theWit, located at  State and Lake Street, is an excellent location due to its proximity to several Chicago attractions, State Street shopping, the Theater District, and public transportation.   (State/Lake L stop connects several transit lines and is steps away).

Turn right once you leave theWit; cross Wacker Drive, and you’re right at Chicago Riverwalk and several excellent eating places.

This modern-looking hotel with its cool mixture of glass, steel, and concrete has a lot to offer the solo woman in town for a bit of fun.


The rooms are stylish, and you can have a choice of a classic or spa guestroom.  Or do it up fancy and go with either the junior, luxury spa or paramount suite.


For more information on hotel accommodations in downtown Chicago, read my post, “Where to stay in Chicago: An insider’s Guide” by clicking here.


If you fly in on a Friday do happy hour Chicago-style

The Loop area empties quickly after business hours. This time of day has always fascinated me.  If you’re not used to the massive wave of people trying to get to their trains (or happen to be swimming against its current) it can be overwhelming. This is when you will see native Chicagoans at their rudest (and we’re not usually offensive).  Get out the way…park yourself somewhere at a happy-hour and wait until the wave passes.

Here are some suggestions:

  • theWit on the Roof – after check-in, take yourself to happy hour on the roof of theWit – click here for more info
  • Fisk and Co – 225 N Wabash, Happy Hour: 4 pm – 6 pm – $1 Oysters
  • Berghoff – 17 W. Adams – Lower Level, Happy Hour: 4 pm – 7 pm – $4 Draft Beer, $6 Well Drinks, $7 House Wine
  • Vol. 39 at Kimpton Gray Hotel – 122 W. Monroe, 2nd floor – Happy Hour: 3:30 pm – 5:30 pm
  • The Bar Below – 127 S State St – Happy Hour:  4 PM – 6 PM; $4 Draft Beer, $7 Well Martinis, $6 High Balls

Top five things to do in Chicago this weekend

So, you’re all checked in, and you’re brimming with excitement!  What should your next move be?  What to do in Chicago this weekend?

1.  Take a tour – There is a tour for everything in Chicago.  But you only have a weekend.  Here are the tours I recommend doing this weekend.

Architectural Boat Tour – Everybody and their momma have an architectural boat tour in Chicago.  There’s so many of them!  I’ve taken a few of those architectural boat tours, and they’re all good.

But hands down the best Architectural Boat Tour is the done by the Chicago Architecture Foundation.  Cruise the Chicago River on the “First Lady” and learn about the history of the city through its architecture.

It is one of the best things to do in downtown Chicago.  If you only have time for one tour during your weekend stay, do the CAF Architectural River Cruise.  Click here for more information.



The Chicago Architectural Foundation also does fantastic walking tours.  Their tours are one of the most popular things to do in Chicago.  My favorite one is the “Elevated Architecture: Downtown “L” Train“.

The price of the tour includes a ride on I believe, the Brown Line (it has been a couple of years since I’ve done the tour).  But it’s a great way to experience the “L” or elevated train, learn about the history of Chicago and its public transportation.  Oh, and you get to see downtown Chicago and its architecture from a different view.


For more information on the Chicago Architectural Foundation, their amazing tours, and the fantastic stuff they do in educating the public about Chicago’s architecture, click here.


2.  Visit a Museum – Museums are another thing that Chicago has a lot of!  It’s going to be hard to whittle my museum list down to just a couple because I have a lot of favorites.

Visit the Chicago Museum Campus (1400 South Lake Shore Drive) – and choose from one of the three museums (you won’t be able to see all of them in one weekend); Field Museum of Natural History, Shedd Aquarium, and Adler Planetarium.

I can’t tell you which one to visit because all three are my favorites.  Sorry.

But if you happen to be in Chicago on a Wednesday evening, swing by the Shedd Aquarium for “Jazzin’ at the Shedd” for drinks and of course, jazz.  The event only happens from mid-June through August every year.  (I know right – why not all year?)

Do you want to save on Chicago attractions and museum tickets?  Purchase the Go Chicago Explorer Pass by clicking here.


Another favorite museum of mine is the Museum of Science and Industry. In 1933, a building that was part of the  1893 Columbian Exposition became the Museum of Science and Industry.

It is located at 5700 S Lake Shore Drive, and not to be missed on your visit to Chicago. It is home to the largest science museum in the western hemisphere. What’s great about this museum is there’s something of interest for people of all ages.

After a visit to the Museum of Science and Industry, you can hang out in Hyde Park a bit and see the University of Chicago (you know, the Manhatten Project?) and the home of President #44.

Grab you a late breakfast at the Original Pancake House (1358 East 47th Street).  I’ve been eating breakfast here for at least 20 years (back when it was located on Hyde Park Blvd).

Food is fantastic – never disappoints and has ruined me for anybody else’s strawberry crepes! And you’ve not had an omelet until you’ve tried theirs. Oh, and pancakes are freakin’ amazing.  Thick-ass bacon…homemade chicken sausage…yeah, I could go on. Go crazy early – I believe they open at 7:00 AM still or after 1:00 PM to avoid the wait.



3.  Go Shopping – Chicago is well known for the fantastic shopping opportunities on Magnificent Mile.  However, there’s a lot of great shopping in the Loop Area as well; most of it located along State Street.  Check out the Target at 1 South State (right down from theWit) – it has absolutely everything.

One day I’ll have to tell you about the time I had to buy a dress, pantyhose, and girdle – from this particular Target. I had arrived at a birthday party, inappropriately dressed in jeans.  Hee hee hee!

Read the “State Street Shopping Guide” by Choose Chicago for more information.

And just in case you need to run to the store for wine or champaign, the following are grocery stores located in the loop

  • Trader Joe’s (1147 S. Wabash Ave)
  • Jewel Osco (1224 S. Wabash Ave) – amazing salad bar


4.  Check out either the Willis Tower (233 S Wacker), formerly known as the Sears Tower or the 875 North Michigan Avenue Building (formerly known as the Hancock Building) –

The former Sears Tower is now the Willis Tower; now named since 2009, for a global insurance brokerage company.  On a clear day in, you can see four states – Illinois, Michigan, Wisconsin, and Indiana.  It is the 12th tallest building in the world and is home to the highest public viewing area in the United States.

The Skydeck located on the 103rd floor of the Willis Tower features the LEDGE.  It is four glass boxes on the western side of the Skydeck for observing the street underfoot.

Admissions:  Adult – $24.00   Child – $16.00

  • Hours: 9 AM – 10 PM from March- September; 10 AM – 8 PM from October- February.
  • For more information, go to

Be prepared for a long, long line before you take the elevator to a floor where you sit through a presentation (the only time you get to sit). Then, you take another elevator up to 103rd floor.

The views are breathtaking up there, and if you don’t mind waiting (again), you can check out the LEDGE.

Recommendation: You will be on your feet the whole time so wear comfortable shoes.  The only seating is a metal bench near the bathroom.

photo by the social tourist


The 875 North Michigan Avenue building is a 100 story skyscraper is the 4th largest building in Chicago. The 360 Observation Deck at the Hancock building…er, I mean the 875 building has the TILT attraction which is a series of floor to ceiling windows that slowly tilt outside the building to 30 degrees.

There is a charge for the TILT of $7.00.

If I had to choose between the two buildings, I would go with the less touristy, shorter wait at the 875 N. Michigan Avenue building.  Grab a drink, find a seat on the wooden bleachers, and take in the best views Chicago has to offer.






5.  Check out one of Chicago’s professional sports team – Chicago is a city that is extremely passionate about sports.  No matter what time of year you choose to visit Chicago you can find a sporting event of some type.

Chicago Bears – You can see the Bears play football at Soldier’s Field (1410 Museum Campus Dr. – Downtown Chicago Loop).   Super hard to get tickets unless you know someone who knows someone’s boss that has company tickets.  For more information on the Chicago Bears, go to


Chicago Cubs – The Chicago Cubs play at Wrigley Field (1060 W. Addison St. – Chicago neighborhood of Wrigleyville), one of the last remaining old-school baseball fields left in the United States. For more information, click here.

Going to a Chicago Cubs game is like hanging out in the neighborhood with all your friends.  It’s extraordinary.  If you can’t score tickets to the Cubs, then hang out at one of the many bars in the area.

My favorite neighborhood bar for watching the Cubs? The Twisted Vine (3530 North Halsted)


Getting to Chicago



If you’re flying into Chicago, remember there are 2 Airports!

Two airports serve the Chicagoland area; Chicago O’hare Airport (ORD) and Chicago Midway Airport (MDW).  You are going to have plenty of ground transportation options once you land. However, the fastest and cheapest way to get downtown is by public transportation. Both airports are easily accessible by public transit; the Chicago ‘L’ trains.

Traffic from the airports is horrible unless you fly in very early or late (after 7 PM).  Unless you love sitting in mind-numbing traffic, I recommend taking the ‘L.’  During rush hour (6 AM- 10 AM and 2 PM – 6:30-7PM), it can take up to 2 hours to reach downtown from either airport (even though MDW is a lot closer to downtown).



Public Transportation

Chicago has one of the best public transportation in the world.  Buses run every 10-15 minutes depending on the route.  Trains run every 7-10 minutes during the day and every 10-15 minute after evening rush hour.  For more information, go to


Recommendation: Google Maps is handy in navigating Chicago public transportation.


Other means of getting around Chicago include Uber, Lyft, or Taxi.


Parking downtown Chicago:   Should you decide to drive in – Parking in downtown Chicago is expensive.  I’m talking $45 a day, with no in and out privileges at downtown parking garages.

Street parking downtown is metered and costs about $6.50 per hour.  Meters accept credit cards, or you can use a parking app.  I recommend reading “Parking in Chicago” by Local Tourist for a great breakdown of parking in the downtown area.


For more information on hotel accommodations in downtown Chicago, read my post, “Where to stay in Chicago: An insider’s Guide” by clicking here.


Are you thinking about taking a trip to Florida?  Consider checking out St Augustine, Florida, click here to read my post.


Are you looking for a travel guide to Las Vegas?  Click here.

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