Flight
O'Hare is one of two airports you can fly in to. If you fly into ORD you can take the blue line CTA train right into the city. The train from the airport to any of the stops to the city is a flat $5 and it takes approximately 1 hour to get to the loop. A taxi cab from ORD costs approximately $40 and will take 40min-1 hour depending on traffic. You can call Ubers and Lyfts to the airport, that will be closer to $30.
Flight
Midway is one of two airports you can fly in to and is home to all Southwest Airlines flights into & out of Chicago. If you fly in to Midway the CTA orange line train goes straight into the city. The train from the airport to any stops in to the city is $2.25 and it takes approximately 45 minutes to get to the loop. A taxi cab from Midway costs approximately $40 and will take around 25-40 minutes depending on traffic. You can call Ubers and Lyfts to the airport, that will be closer to $25.
Train
The 'L' can get you around Chicago, depending where you are going. Trains go to and from both airports and the city and are a nice option (for $5 or less). Check out the travel time and leave some extra time if you are taking the train to the airport. (It takes about 10 minutes to walk from where the train lets you out to the ticketing desks at the airport - all inside at the airport, but still allow for some extra time.) Trains are also a nice way to get to different neighborhoods in the city.
Rental Car
Uber and Lyft are good options to get around in Chicago. Both are (usually) faster than taking the CTA and a bit easier if you aren't familiar with the train.
Hotel
Use this link to book the hotel - https://book.passkey.com/go/PriceArandWeddingAloft