Revisiting Chicago – and why the third visit to a city is often the best

Revisiting Chicago offers a new perspective. Explore why the third visit to a familiar city often proves to be the most rewarding experience.

First time vs second time in Chicago

The first time I visited Chicago, I was thoroughly bowled over. The skyline got me giddily excited, the vibe seemed right up my street, and I found just about everything I threw myself into fascinating.

The second time, however, was a little different. I had a good time, and I still really liked the place – but that virgin’s sense of wonder had been dulled a wee bit.

This, I guess, is only natural. The thrill of seeing or doing something for the first time is always going to trump the sensation of the repeat experience.

Visiting Chicago a third time

The third visit, however, was very different. This time, there was a certain degree of familiarity. For decent chunks of town, I didn’t need to consult a map. I also had no real need to go back to some of the more obvious tourist attractions. Navy Pier (home of the Chicago Children’s Museum and Centennial Wheel) and the Willis Tower were hardly on top of my priority list – and that bought me plenty of time to go hunting in less obvious neighbourhoods that I’d not have considered before.

Pilsen, Hyde Park and Logan Square

I ended up in Pilsen, which has long been a Mexican ‘hood, but has got a little influx of the creative crowd. As it turns out, it’s a lovely place to mooch around, looking at murals, feasting on tacos and rummaging around vintage clothing shops.

I also ended up in Hyde Park on the South Side. That’s where you can pass the university lab where Enrico Fermi and co pulled off the first man-made nuclear reaction, then go past Barack Obama’s house and ogle Frank Lloyd Wright architecture outside of guided tours in Oak Park. Hyde Park feels nothing like the Chicago I already knew – it’s bookish, ever so slightly reserved and has a strong African-American background.

Then there’s Logan Square, which is allegedly the hipster area, but pulls off the hipster thing with a refreshing lack of pretentiousness and attitude. It’s tremendous to bar-hop round, and there’s an unthreatening warmth as you’re doing so. Nobody is there because they feel they ought to be seen there. They’re there because they like being there.

Falling in love with Chicago again

After five nights of poking my nose into different areas, I found myself head over heels in love with Chicago again. And this time it was love, rather than lust. I’d gone beyond the initial instinctive attraction to get a broader appreciation of more nuanced parts of the personality.

This isn’t a one-off, however. It’s a pattern I’ve noticed with other cities. With the likes of Berlin, Prague and Edinburgh, I’ve gone home raving about them after the first visit. Then the second has been relatively lacklustre, and the third brilliant again.

Sequels vs reboots

I think this is a question of approach. The first time, you take it as you find it. On the second visit, however, there is a temptation to relive the brilliant time you had on the previous visit. And doing pretty much the same again is never going to quite bring back the same feelings.

Therefore, the third time is about deeper exploration and re-evaluation. It shows the city in a new light and taps into the aspects that don’t rush to the surface. There are few better ways to rekindle the passion.

There’s perhaps a lesson in this. There doesn’t need to be that mildly disappointing second visit – just go in with the approach that you would have on the third trip. Don’t go for the sequel – go for the reboot.

Things to do in Chicago’s Loop

Chicago’s Loop is the city’s historic and commercial core, with many of its best known sights concentrated within a compact, walkable area. It is easy to link several of these attractions in a single visit.

Willis Tower Skydeck
One of the most recognisable buildings in the Loop, the Willis Tower offers expansive views across the city and Lake Michigan. The glass ledges projecting from the upper floors are a major draw for visitors.

The Art Institute of Chicago
Located at the eastern edge of the Loop, this museum houses an internationally significant collection ranging from Impressionist paintings to modern design. It is one of the city’s most visited cultural attractions.

Millennium Park and Cloud Gate
Bordering the Loop to the east, Millennium Park is known for its public art, open spaces and outdoor events. Cloud Gate is the centrepiece and one of the most photographed sights in Chicago.

Chicago Theatre
On North State Street, this historic theatre is famous for its illuminated marquee and ornate interior. Even if you are not attending a performance, the exterior is a notable Loop landmark.

Chicago Cultural Center
Opposite Millennium Park, this former library building is worth visiting for its architecture alone, including an impressive Tiffany stained glass dome. It regularly hosts free exhibitions and events.

More Chicago travel

Other Chicago articles on Planet Whitley include:

• Tribune Tower – the building that stole the world.
• Kayaking along the Chicago River.
• Why you should do a Chicago architecture walking tour as well as a cruise.
• Touring Chicago’s gangster heritage.
• Experiencing different pizza styles in Chicago’s West Loop.

For more Chicago activity and experience ideas, head here.

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