What’s your price point in terms of hotel? Anything on magnificent mile will cost you, but, you’re in the heart of it all. The Hilton on N Michigan Ave is a great option. Far enough away from State St where it’s a bit calmer, and possibly a little less expensive, but just 10-20 minute walk from literally everything. Blocks away from walking to the Lake.
There is a breakfast joint called “Yolk” on Michigan Ave. Def go there! It’s delicious! Be ready for a wait time on the weekend.
If your a fan of steakhouse, Gibson’s or Hugo’s Frog Bar and Fish House on Rush St is a must!
If you want Italian, Carmines, also on Rush St is delicious.
Go to the John Hancock building and relax in the LOUNGE area, not the restaurant. The restaurant charges tons to eat there because you have 360 view of the city, BUT, the food is NOT WORTH IT. Going up one level to the lounge will give you the same view for fraction of the cost. Go there late at night for a drink or mid afternoon for drinks and an appetizer.
Ride the Ferris Wheel at Navy Pier. It’s literally just that, a huge Ferris Wheel, but SO something to do in Chicago. 🙂 It’s like 7-8 minute ride and you get to see a nice view while up there. Cost is like 5 bucks. A friend of mine proposed to his girlfriend when they were on the ride, which I thought was adorable.
Go to the Shedd Aquarium, it’s awesome.
DO NOT go to the Field Museum unless you’re a BIG buff of anthropology and all that, otherwise, you’re gonna get bored.
Lincoln Park Zoo! Free zoo near the Lake. It’s worth checking out.
If you’re there in the Summer, go to a Cubs game in Wrigleyville! Yes, the team sucks, big time, but the ambiance and atmosphere there is one of a kind! Relax either before the game at a bar/grill, or go into one of the bars/restaurants nearby after the game for dinner. Even if we’re losing by ten, it’s a great place to be.
The Art Institute of Chicago is a great museum. Check it out and google when they have free admission days. Last I knew, they were on Tuesday. Could be different now.
Yes, take a boat ride, the sunset one is nice. Architecture tour is nice but could get slightly boring, but maybe that’s cause it’s my city and I’ve heard it all before.
You have to go to Portillos! A fast food restaurant joint that’s fancier than a McDonalds or anything like that. The beef sandwich there is delicious, and the cheeseburgers! The fries, the hotdogs, everything really. You can’t go wrong ordering anything from there. I’m moving out of Chicago after I get married and this place is one that I know I’m gonna miss.
When you’re at Navy Pier, rent bicycles. You can rent them for as long as you want. Take a bike ride along the Lake on a nice summer day. The trail along Lake Michigan is a beautiful one to bike, run, even walk along during the day or quiet summer night.
If the broadway show Wicked is in town when you are here, go and watch it!
Most people don’t come to Chicago without visiting the Sears Tower, so you’d want to check it out. Tallest building in the city, and they built this plank that comes out that you can stand on, with the city beneath you, it’s pretty cool. View is slightly similar to John Hancock, though you are much higher up so you’ll see more. On a clear day, you can see border of neighboring states. It’s expensive to go up there and I’ve gone on more than one occasion with out of towners when wait time was 2+ hours! So, if you are going to go, go early on a weekday, or a little before they open on the weekend so the wait time isn’t crazy bad.
That’s all that comes to my mind right now, if I think of anything else, I’ll let you know. PM if you have any questions. Happy to help! I love my city tons, and love talking about it, ha. 🙂
ETA: Oh, if you plan on riding the L (our subway system) to get from place to place (for example, if you decide to go to a Cubs game, hop on the L to Wrigleyville, DO NOT take a cab, will cost wayyy too much), buy an all-day pass or I believe a 2 day pass is available. It’s comes out cheaper if you’re gonna use public transportation to get around rather than paying per ride and with the pass, you can ride as many times as you want, along with using it for bus rides, if you buy the combination one. Note, watch your bag/wallet on the L. Just keep it in your lap.
Oh yea, and also check out Millennium Park, The Bean, and Buckingham Fountain. At 9 pm, the fountain does a water works show which is nice to see for the first time. All three of these places are roughly around one another. Oh, and in the summer months, there’s a firework show every Saturday night. So if you’re going to Navy Pier, go on Saturday and watch the show at night.
If you want a nice, quiet ambiance with a nice view of the city, take one of the dinner cruises that leave from Navy Pier.