Visiting Chicago - what not to miss?

In September I will be visiting a friend doing his exchange semester at U of Illinois : Urbana-Champaign for about a week. Looking for some recs for:

  • Chicago - will probably get a hotel and spend a long weekend in the city - where to eat/drink/see/go out? (Big fan of house music so would love tips for this) 
  • Urbana/Champaign or Illinois in general - will probably rent a car for a few days as well, any trips worth doing in the state?

We are both from Northern Europe in mid-late 20s. I've spent a good bit of time in the US before but mainly in California/South

All tips and opinions would be helpful and very appreciated.

Comments (33)

Aug 17, 2022 - 7:02am
quire2, what's your opinion? Comment below:

of course, this is a given

Aug 17, 2022 - 4:41pm
Pierogi Equities, what's your opinion? Comment below:

Absolutely raving reviews on Google Maps, highly recommend

Quant (ˈkwänt) n: An expert, someone who knows more and more about less and less until they know everything about nothing.

  • 2
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Aug 19, 2022 - 5:36am
BigKahunaBanker🏄🍹🍔, what's your opinion? Comment below:

Yeah, especially if you're a bad mother from 63rd who's smoking on Von lmao

...and the Truth shall set you free
Aug 17, 2022 - 12:11am
JustineTobinFootMassage, what's your opinion? Comment below:

Saw this late but definitely the Riverwalk. Also, I had some great fucking food at a restaurant in West Loop (courtesy of my firm lol shoutout intern perks). Lotta great foodie places in general and of course their deep dish pizza is crazy. It's like deliciously chewy (not sure if thats the best description) and there are two super well known pizza places. Can't remember the names though. And of course, go see a Cubs game. Fucking baseball games are so fun dude one of the funniest things I saw there was people stacking the beer cup snake (not sure if thats legal lol). But yeah baseball game atmospheres are so sweet definitely something I will go experience again.

Most Helpful
Aug 17, 2022 - 5:03pm
Pierogi Equities, what's your opinion? Comment below:

I think [Deal Team Six] is from/lives there and would have great advice. Generally WSO loves Chicago and for good reason imo, it's a great city, especially when comparing costs relative to NYC, SF, DC, etc. Here's some stuff I checked out when I went earlier this year:


  • Sears Tower (there's an elevator to a bar in the John Hancock tower that I think is free though)
  • Riverwalk
  • Millennium Park/Grant Park/Bean/that whole area
  • The 606: elevated walking/biking trail in Logan Square/Wicker Park
  • Walking down the Magnificent Mile
  • If you like architecture, you should research specific buildings which are generally in the Loop or close. The architecture boat guides will discuss some of them in detail
  • This is specific to me but Polish Cathedral style churches (Wikipedia article about it) which are beautiful and generally in the northwest part of the city. Also found in Pittsburgh, Milwaukee, Buffalo, etc.
  • Navy Pier is nice to walk along but kind of overrated imo
  • Parks and boulevards linking up the Chicago boulevard system (Wikipedia article about it) are also interesting
  • Logan Square and Wicker Park are younger neighborhoods with great places to eat/drink, but I'll let others with more knowledge chime in about this


  • Cubs game
  • Architecture boat tour
  • Various museums (Field Museum, Museum of Science and Industry, Shedd Aquarium, etc.).
  • Rent a bike and ride on the Lakefront trail
  • Make your own walking tour of the Loop if you're into architecture for stuff that's not covered on the boat tour (highly recommend finance stuff like the Federal Reserve Bank, Merc, Board of Trade, and other ones like the Sears Tower, Tribune Tower, etc.)


  • Pequod's Pizza, really good
  • Portillo's for Chicago-style hot dogs
  • Any place serving Italian Beef (Wikipedia article about it)
  • Basically anywhere in Chinatown
  • Since Chicago is such a large city, you can find pretty much anything you want. Since your friend is in school still and probably wants to save money, here's the Bib Gourmand entries for Chicago from the Michelin Guide
  • I don't know how accurate this is, but someone told me that Chicago has great seafood places due to its airports


  • Goose Island taproom, I think there's 2 at least
  • Many bars are open to 3-4am which is great

Quant (ˈkwänt) n: An expert, someone who knows more and more about less and less until they know everything about nothing.

  • 12
Aug 18, 2022 - 9:47am
Brio, what's your opinion? Comment below:

This is fire. I'd add some stuff to do in Old Town and Lincoln Park:

- LP has the free zoo that you can walk through in like an hour and is near the water.
- The J. Parker is a chill rooftop in LP you could hit for a drink after walking around the zoo.
- Bars on N Wells in Old Town. There are several good ones. I like Benchmark & Woodies but you should just hang out wherever U of I ppl go. 
- Second city for improv comedy if you're into that.

Not mentioned in Millennium Park is Cindy's rooftop, its touristy AF but the view/scene is good. 

  • 3
Aug 19, 2022 - 4:03pm
Pierogi Equities, what's your opinion? Comment below:

- LP has the free zoo that you can walk through in like an hour and is near the water.

Can't believe I forgot about that, the zoo is really good, +1. After being there and especially the DC zoo, both of which are free, I've really been spoiled and can't go to a paid zoo.

Quant (ˈkwänt) n: An expert, someone who knows more and more about less and less until they know everything about nothing.

Aug 18, 2022 - 12:53pm
MacroJunkie, what's your opinion? Comment below:

Second the architecture boat tours, especially if the weather is nice. West loop is a great up and coming area with a lot of nice bars and restaurants. I'm partial to Italian, but here are a few of my favorite restaurants in the city:

  • Forno Rosso - Italian pizzeria in West Loop
  • Monteverde - general Italian. Some of the best spaghetti I've ever had.
  • RPM Italian - more Italian/American fusion, nightclub-esque vibe, good food right in the middle of downtown
  • Eataly - very modern, affordable, several small Italian restaurants in one building with grocery store, dessert shops, etc.
  • Gilt bar - English/Scottish themed upscale bar/restaurant. Great food and atmosphere.
  • Au Cheval - Michelin star burger restaurant in West Loop. Not too expensive, but usually has a crazy long line.
  • Shanghai Terrace - upscale Chinese restaurant in the Peninsula Hotel downtown. Most authentic Chinese food you'll find in Chicago.
  • Happy Lobster Food Truck - Chicago has a lot of great food trucks, and this one moves around, but they sell really great (and cheap) lobster grilled cheeses. 
  • Grand Lux Cafe - solid American-style restaurant by the same people as the Cheesecake Factory located right in the middle of downtown. Great chocolate lava cakes.
  • Three arts club cafe - small restaurant in the middle of the Restoration Hardware store in Gold Coast. Beautiful decoration and great food.

As far as sights to see, I'd recommend:

  • Gold coast/Lincoln Park - beautiful upscale art deco-style apartments and one of the biggest parks in Chicago.
  • Milennium park
  • Navy pier
  • Riverwalk
Aug 18, 2022 - 2:30pm
LeveredLegend, what's your opinion? Comment below:

If you're lucky, you can get 800 LBs of poop dumped on you while on the architecture boat tour by the Dave Mathews Band tour bus. 

Aug 18, 2022 - 10:31pm
Deal Team Six, what's your opinion? Comment below:

Appreciate the call out [Pierogi Equities], hope all is well on your end. 

Couple disorganized thoughts from a sleep deprived local: 

U of I Urbana Champaign is nowhere near Chicago and there isnt much to do aside from party at UIUC. As a student abroad, I imagine you are strapped for cash. My advice is to enjoy the house parties and hit the bar scene. If your friend who is abroad is friends with guys in fraternities, this will help tremendously. Why?

1. They probably know of somewhere to have fun every night of the week, including "dead" nights

2. They likely know AT LEAST 1-2 bartenders who will hook you up with the cheapest drinks you will have at any bar during your entire time in Illinois. I went there multiple times and visited different friends who were all in Greek life, and they each knew 3-10 bartenders. UIUC is the biggest greek life school I know of (something like 80+% of students are in houses). If you have a connection with a bartender, you will be paying $1-5 for every drink you order. I dont want to date myself but when I was there a few years ago I dont recall paying over $3 for anything, courtesy of fraternity / sorority connections. 

3. The talent at UIUC is as good as it could be given it is a cornfield in Illinois. A ton of beautiful girls and the bars are pretty packed with them. 

Chicago is fun but I need to know your price range for better advice. The house artists typically play at the more expensive places. Look into who is DJIng / performing at sound bar, spy bar, TAO (super douchy and clubby where drinks are overpriced, but great house artists), or maybe Joy? Not really my scene so I am not super close with that. 

Wrigley Field. If youre looking for a good touristy attraction when the weather is solid, you should definitely go to Wrigley. You can buy tickets for next to nothing. Get a dog, beer, and enjoy a mediocre sports team. Go with a few friends and you cant have a bad time regardless of the game itself. 

Cheaper Bars. Much less close with the night life scene than I used to be, but a couple fun cheap bars by location: 

1. Halligans - Lincoln Park. Not exactly a popping night life scene in the general area, but many low key bars in the area. Last time I was on there on a week night they had $2.50 beers, meaning in order to pay with a credit card you need to buy around for the boys ($10 minimum). You are easily a $20-30 uber away from any good place to actually go out. 

2. Galway Bay -Lakeview / Lincoln Park border. Top notch dive bar with cheap drinks, and every drinking game you could want. I am talking golden tee, darts, pool, all the way through Mario Cart on N64. Not a good scene to meet girls but a great place to start a night out. 

3. Woodys on Wells - Old Town. Underrated bar that is less crowded in one of the most popular areas to go out for early 20-somethings. One of the only bars I a surprisingly high number of girls come up to me and started hitting on me at. If you want to go to a more "popping" bar you can easily walk to Pour House, Benchmark, Fireplace, etc., all bars within 1-2 km. Those bars were when I went in my early 20s and will likely be more your scene. 

4. Cindys - The Loop (heart of Chicago / financial district). One of the best views of Chicago. Extremely cool layout and very fun to grab a drink at. Drinks are costly, but the view and environment is worth it. 

Suburb Beaches (North not South of the city): Suburb beaches > city beach any day. Beaches in the city are mobbed and underwhelming. Google maps some beaches about ~20-40 miles north of the city to find some really low key spots with better sand, better company, and in general, one fifth as many people. If you PM me I can name my absolute favorite beaches, but dont want to advertise them to the local public as they are super low key. Most importantly, dont go south looking for a good beach as that will take you toward a less desirable / dangerous part of the city.

If you have any other interests just lmk and I can recommend other things to do, but thats my general advice. Many may disagree on some of the points but I guarantee most locals who have been to the places I recommended will agree. 

Aug 22, 2022 - 6:55am
quire2, what's your opinion? Comment below:

This is amazing, thank you very much.

In terms of budget - I am working in IB atm, and just got a decent bonus and will be moving to the buyside after my trip, so I def have some cash to spend. My friend may be on a lower budget given he is in school, but has also worked full time for a few years before and alongside his degree (European things lol) so he has some wiggle room.

Yep, aware that Urbana-Champaign is in the middle of nowhere but we'll probably just chill and go out a few nights and then go to the city for a few days as well. 

Noted on the Greek life, will let my friend lead the way and hopefully has a decent network by then (not sure what the perception is of someone who is a couple of years out of college and hangs out at college bars lol)

Aug 21, 2022 - 8:48pm
AnonymousGoon, what's your opinion? Comment below:

This is a fantastic list. I lived in Chicago for a few years and will probably share this next time somebody asks for recs

I'll add one other thing. During the summer / when it's warm, rent a bike and ride along the lakefront trail. I'd usually suggest starting near navy pier (it's easy to get bikes there) and riding south, either to Northerly Island or further and back. The lakefront bike trail is really top notch -- it's well-maintained, scenic, and super flat / easy

Aug 22, 2022 - 9:52am
Pierogi Equities, what's your opinion? Comment below:

definitely agree on the bikes, I did that last time and forgot to mention that too. With a nice breeze and low humidity, there's nothing better.

Quant (ˈkwänt) n: An expert, someone who knows more and more about less and less until they know everything about nothing.

  • 1
Aug 18, 2022 - 1:41pm
grantmeaname, what's your opinion? Comment below:

The field museum is superb.

The architecture foundation that does the boat tour also does great walking tours if that's your thing.

And can it ever be?

  • 1
Aug 18, 2022 - 2:28pm
LeveredLegend, what's your opinion? Comment below:

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Aug 19, 2022 - 10:49am
Hugh Myron, what's your opinion? Comment below:

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