You can choose to fly into Midway (MDW) or O'Hare (ORD), depending on the airline you are flying. Both are ~30-45 min drive to the city.
Ubers and taxis are readily available from the airport. Renting a car will be more expensive than Ubering or walking around (parking is expensive). Or, if you're feeling adventurous, you can take the CTA (train) from the airport right into the city.
We don't have any room blocks but this hotel is our recommended affordable place to stay.
We don't have a room block at LH, but this is where the bride and groom will be staying. We recommend LH if you are looking for a fancier option with a fun view. Their rooftop is Ang's favorite view of Chicago!