My first trip to Chicago, I was sixteen years old. That gives me 22 years worth of anecdotes and experience on what’s worth your time and what isn’t. I know it better than any other city, and though I’ve never lived there, it’s got a special place in my heart.
I’m sure there are things that natives know about that I don’t – but I have a feeling that even if I did, they’d prefer it if I kept the secret-revealing to a minimum. So, I’m just gonna highlight the things that are must-sees and give you a few tips for getting around easily.
1.Getting around easily.
Do not, under any circumstances, attempt to drive everywhere. It’s a lesson in futility for one, because you will spend more than half your time finding parking, or you will spend a sizable amount of your budge just paying for it. Park somewhere and stay put. Or better yet, take the train in from the suburbs. There are plenty of safe places to park your car. Next, get a CTA pass. You can get 1, 3, 7 or 30 day passes that you load onto a Ventra Card. You can use it for the buses or for the El.
If you have time, just ride the loop. It’s a nice look at downtown Chicago.
Note: The transit map can be a little daunting. Get the CTA app and make your life easier.
2. Where to Stay
This depends on what you are in Chicago to do. But I always recommend staying in either the Hilton or the Club Quarters. They are both on Wacker Dr – one to the west of Michigan Ave, and the other to the East. When we take our kids we stay at the Hilton, when it’s just me and my husband, we stay at CQ. We’ve also stayed at the Congress Plaza – and whilst I love the lobby, I wouldn’t recommend it. Wacker & Michigan are central to major bus lines that will take you everywhere, and they are withing walking distance of several El stops.
I love the Club Quarters bc its right on the river across from Trump Tower. Gorgeous views of the city.
We’ve also stayed in Boystown – super nice area. Felt very safe and it’s within walking distance of Wrigley Field.
3. What to Do
Now that’s the question isn’t it? We’ve done just about everything, and it’s all worth the money. Except maybe…no – it’s all been worth it. Here’s a few of our favorites.
Chicago 360 – formerly known as the John Hancock Observatory. I like this better than the Sears Tower (I know it’s been renamed. I don’t acknowledge it). The museum and lakefront views make it the better choice.
Shedd Aquarium – Best aquarium ever. Get the full ticket, because you don’t want to miss the Oceanarium.
Field Museum – Mummies and Dinosaurs and whatnot make this a great place to visit with the kids.
Museum of Science & Industry – Very cool place. Kids loved it.
Art Institute of Chicago – Worth the time. Very nice facility, great art. The people working there are a little condescending – but worth it anyway.
Navy Pier – you have to go to Navy Pier. Nothing else to say. Iconic.
Water Tower – One of the only buildings to survive the infamous fire of 1871 – it’s worth a look. On my first trip to the city, I stopped at the fire department across the street and got shirts for my family and my two best buds (they were firemen, as was my dad). Nice area of the city.
Millennium Park – you have to go see the Bean.
Grant Park – If nothing else, you need to visit the site of so many Lollapalooza concerts. One year we were in town for a Bears game, and after we walked through the park. We got to hear Pearl Jam. It was killer. But really check it out, it’s a lovely park.
Buckingham Fountain – because Married with Children (duh!)
Lincoln Park Zoo – one word…FREE… that’s all you needed, right?
Wrigley Field – if it’s baseball season, and the cubs are home, you need to go to a game. I know they altered it, and it’ll never be the same, but this is my favorite field of all time.
Soldier Field – same for Da Bears. If they are in town, you should go.
Architecture Cruise – You get on by the Wrigley Building and it’s super interesting. I’m not a tour kind of gal, but I enjoyed it.
American Girl Store – If you have a daughter, you must.
Legoland – We haven’t yet, but it’s on the list.
4. Where to Eat.
Depends on what you like. But if you are getting a pizza, and you get it from anywhere but Lou Malnati’s you will regret it.
Lou Malnati’s – the iconic deep dish you’ve been looking for. Don’t buy what anyone else tells you – this is the real deal. We crave it. The one on State is bigger, but I like the one on Wells better. (Giordano’s is crap. Trust me.)
Ditka’s – not just for the Pot Roast Nachos either. It’s a classy joint with some killer food. And the service is impeccable. (But seriously, those Pot Roast Nachos are to die for.)
Navy Pier – you’re going here anyway, better get something to eat.
Chicago Dog – My favorite hot dog stand in the city is between Soldier Field and The Field Museum. Don’t ask for ketchup – they’ll make you dance for it. Actually, I think they do that everywhere, but I like this place.
Irish Pubs – We’ve eaten at least a few Irish Pubs downtown and all were fantastic. One was on Wells, the other on State, but I can’t recall their names.
5. Final recommendation – get a CityPass. It gives you admission to five attractions (almost all are on the list above). Totally worth the money AND you get a FastPass that let’s you line jump when you need to.
If you’ve got anything I’ve forgotten, leave a comment. We’re always up for awesome things to do in the city!