Hotel
The Robey hotel is located against the backdrop of Wicker Park and Bucktown's bustling six-corner intersection. It is a lively neighborhood with plenty of restaurants and shops to walk to and has easy access to the "L" ( for non Chicagoans this stands for the elevated train system aka our metro). There is a rooftop restaurant as well as a pool. It is about a 7 min uber/drive to our house or a 25 min walk (1.2miles)
Hotel
This hotel is located in the Wicker Park neighborhood. Jennifer enjoyed having cocktails and now mocktails at the rooftop bar drinking in views of the Chicago skyline. This is an 8 minute uber to our house or a 38 minute walk (1.8 miles)
Hotel
Looking for more of a fun downtown experience? The Gwen is one of our favorite hotels to also visit while in town. It is located on Michigan avenue and easy access to all the downtown Chicago tourist attractions not to mention shopping! It also has a cute rooftop to enjoy. It is a 19 minute uber/drive to our house (4.9 miles)
Flight
We find flying into O'Hare to be the easiest and closest for us. However if you are staying downtown you could look into Midway if that works better from your travel location.
Flight
Chicago Midway is generally a bigger hub for southwest if that is more convenient from your city.