Samantha,

A good place to start is at Buckingham Fountain walking north to the Bean at Millennium Park.  Hug the lake front for great views.  Then, a walk along North Michigan from the Wrigley Building to Water Tower is nice featuring many shops.  A trip to Navy Pier is also a nice diversion.  Chicago has many fine dining restaurants but I am not the right guy for that topic.  For Chicago food, pizza, hot dogs and Italian beef are signature dishes.  While it is a chain, Portillo's is great for dogs and beef.  Tons of pizza places.  For a culture the Art Institute is outstanding and on the path I outlined above.  The Cubs are in town so a trip to Wrigley Field is a must for sports fans.  (I am sorry the board is so dead)  Enjoy!!

Cubs17

You can't come to chicago with out a getting a good Chicago hot dog. One of my favs is Chicago Oven-Grinder. Thank me later - YUM!

Lots of fun in Chicago!

Welcome to Chicago Samantha!

Millennium Park is a great start to visit. May I suggest picking up a GoChicago Card or Citypass to make your experience worth your while. The pass can be pricey, but worth it for the attractions included such as going up to the Observation Deck of the former Sears Tower aka Willis Tower, or the John Hancock. For people watching, River North or the Viagra Triangle is the place to visit. The city offers many restaurants but can get expensive unless your date is willing to pick up the tab. For an interesting tour, check out the Gangster Tour which will take you through parts of Old Chicago or a haunted tour, there is also the double decker buses which give nice tours or if you are into buildings and architecture, a river cruise would be fun to go on as well. Most of the museums are fun and interesting, however the Museum of Science and Industry is a bit far from the downtown. Slowly the night life is coming back along with local dives and some of the music festivals. I hope you have a great time here. If you are looking to pick up guys, then hit up the Viagra Triangle.
Enjoy!

Double check and double check

Not sure why no one has mentioned

Early check in at your hotel......A toss up...  

Restaurants may need reservations or long wait times  
Uber/lyft prices are thru the roof  
Uber/lyft  wait times are just unforgivable. Plan ahead

Perhaps you got a rent a car for your trip....Those prices gave me a headache...among other things

Get a ventra card... if need be..

Other than that..your trip should be fine..

Hello Samantha,

I suggest visiting the Museum Campus. It's about a 45 minute walk from downtown along the lakefront. During the day it's full of people watching opportunities and you have a lake view. The campus has three museums Adler Planetarium, Shedd Aquarium and the Field Museum of Natural History (The best one in my opinion because of its variety.

As for stay: The Sheraton Grand is nice, on the river and pre-covid was busy enough that no one paid attention to you

Food: Star of Siam, good Thai food at a reasonable price. On the much higher end, Eddie V's or STK (both steakhouses)