Chicago is packed with so much fun things to do like you’d expect from every other major cities. It’s quite easy to get caught up in the so many tourist traps. It is even easier to miss out on local favourites that come with the city, especially in a really big city like Chicago, where options available to visitors are seemingly endless.

Looking for what to do in Chicago? You can choose fun things ranging from the world-class museums, vibrant shopping districts and the ample nightlife venues, just to mention a few. Some of these fun and amazing places to unwind, learn and relax will be shared in this piece.

Chicago Parks District offers a serene atmosphere for fun and relaxation:

Chicago parks district is loaded with so much fun things to do. It is the unarguably the oldest and one of the largest park districts in the US. It operates 580 parks that stretch out across 8,100 acres of municipal parkland. I bet you, you will be missing so much fun not to pay at least one of them a visit for a fun urban nature escape. Lincoln Park and Grant Park actually get most of the visitor’s attention.

Take some time to have fun, learn and hang out on Wayne Campbell’s couch and other cool SNL sets

Chicago is endowed with tons of fun and cool museums all worth checking out. The Saturday Night Live exhibit at the Museum of Broadcast Communications is definitely one not to miss because the fun is out of this world. Even if you’re not a fan, the exhibit is so comprehensive that it’s impossible not to be impressed and have great fun.

Hike the glorious 606 and have fun on another level

The 2.7-mile elevated pathway which is along an old railway line passes through neighborhoods like Bucktown, Logan Square, and Humboldt Park, with plenty of cool bars and restaurants along the way to stop off at for fun-filled packages and a little pick-me-up, including Handlebar and Weegee’s Lounge.

It is modelled after NYC’s High Line, The fun 606 urban hiking trail is the best way to see the city’s neighborhoods with a little nature thrown into the adventurous mix.

Take a stroll along the lakefront across a stretch of neighborhoods

Trust me; you haven’t seen Chicago until you’ve viewed Chicago from the lakefront. And guess what? It is free. So you can make it happen by strolling any portion of the 18-mile lakefront path from Ardmore Street to 71st.

Spend a day at Chicago’s beaches

The beaches in Chicago are one of the best things about Chicago summer, you can have fun and enjoy with the less crowded but still centrally located spots such as the criminally underrated Ohio Street Beach. And with on-site Caffe Oliva slinging drinks and fish tacos with the downtown buildings to one side and the equally underrated Milton Lee Olive Park on the other, there is so much fun to be savoured around here.

Devour an Italian beef sandwich

There is no doubt that Johnnie’s Beef in suburban Elmwood Park certainly makes really fine Italian beef sandwich. So if you’re in the city and want to get unique slice of fun, a trip to Chicago’s Little Italy/University Village neighborhood should be top place on your itinery.

Make sure you do the deep dish — the fun way

Ok, so most out-of-towners inevitably inquire about deep dish pizza at some point in the conversation. Pequod’s in Lincoln Park is a great example within city limits, with Burt’s Place out in suburban Grove is more than worthy of a little road trip of fun.

Understand the reason why the Chicago-style hot dog is the only style

It is advisable that you complete the tripartite of Chicago food by taking down a Chicago-style hot dog at a local institution like retro drive-in Superdawg. Or if you’re particularly famished, then you can take a fun trip to The Weiner’s Circle. Just be prepared for the amazing and weird fun wrapped into one; it’s one of Chicago’s most foul-mouthed experiences.

Have a power lunch at Manny’s Deli

Trust me; the Manny’s Deli is so famous that even President Obama had dined there so had President Clinton. It has indeed become a common tradition for about every politician who ever set foot in Chicago. And so should you, don’t you think so? Having a power lunch on a Reuben or beef pastrami in this legendary cafeteria-style diner where business gets done in Chicago offers so much fun that you can’t resist.

Catch some live comedy at the fun-filled Second City

Indeed the second city may be the most known comedy venue in the city, but you can also catch amazing drinking and game performances at The Cornservatory or up-and-coming comics at the Lincoln Lodge – which is America’s longest-running, independently run comedy show — at Under the Gun Theater.

It’s time to get weird at a weird museum

It is true that a trip to the Museum of Science & Industry or Shedd Aquarium is never a bad idea, but did you know Chicago also hosts a Video Game Art Gallery? And also a leather museum with bondage exhibits? More so a creepy International Museum of Surgical Sciences which houses medical artifacts like amputation saws and a plaster mask made from the death mask of Napoleon? Summarily: Chicago has got some really amazing museums, and there’s no shortage of places to get weird or have fun on a rainy day in Chicago.

Pay a visit the South Side to find under-the-radar art

So you may be bored or looking out for what things to do while in Chicago. It is advisable that you head down to the South Side to have fun out at the city’s most underrated art museums which includes the Stony Island Arts Bank and University of Chicago’s Smart Museum of Art. Meanwhile, there’s always something fun and interesting going on – which includes live music band performances and other eclectic underground events — at Bridgeport experimental arts spaces like Co-Prosperity Sphere and Zhou B Arts Center. It is indeed guaranteed that you will enjoy yourself and have fun.

You can explore Chinatown (by foot or by boat)

Guests feel like they’ve entered another world when they pay visit to Chicago’s Chinatown, where a fun food tour seems like as great an idea as anything. You can also have fun checking out a secret ping-pong club in a Chinatown back alley and, for a truly authentic fun-filled experience not a lot of tourists know about, you can ride the water taxi in from Ping Tom Memorial Park.

You can catch a show at any of Chicago’s live music venues

It may be that you’re grooving to indie rock at Empty Bottle or head-banging to punk at Reggie’s, you can never have a dull moment in Chicago’s thriving underground music scene. The Hideout is another fun local gem, and, if that’s not enough, you’ve got plenty of good old-fashioned bars regularly serving up live music as well.

Try a shot of Malort at one of our many dive bars

All cities indeed have dive bars, true! But there is no other city where they are as integral to the fabric of the local culture as Chicago? You can decide to have fun touring them by neighborhood or, if you may want to go off the map, then you can venture into these largely unknown dens of dive bar obscurity.

Dive into the crates at our best local record stores

Chicago is blessed with really large and diverse base of interesting neighbourhood record stores, which will help any out-of-town guest, get a feel for the hood they are exploring. From Reckless Records in Wicker Park to Hyde Park Records in Hyde Park, there are plenty of cool new sounds (and vinyl) on offer from Chicago’s welcoming music head community.

What is the best time to visit Chicago?

So the best times to really visit Chicago is April through May and then between September and October. The main reason for this because the temperature is warm, and a whole lot of festivals take place plus the crowd are manageable. The summer period marks the peak of Chicago’s tourist and festival season, with many travellers from around the country trooping here and eager to take advantage of the warm weather and abundant activities. Although during these seasons the lodging rates are quite higher. Chicago experiences frigid level temperatures from November to March, but if you can hack it, hotel and airfare deals are easy to find.

Summer is unarguably the most popular time to visit Chicago, so you can expect the prices to be at their highest and hotel vacancies to be hard to come by. So while booking in advance is generally a good rule of thumb for Chicago, it especially applies to this time of year – so you can plan on locking down your hotel reservations at least three or four weeks in advance. The average summer temperatures may range from the high 50s to the mid-80s. But the temperatures can fluctuate significantly if there’s a passing heat wave with high humidity or strong breezes from Lake Michigan, so you may pack a mix of clothes. Also, you may expect to encounter some rain in August.



























































