Chicago is a great city to visit any time of year. Fabulous architecture, incredible museums and affordably priced hotels (with no hidden resort fees) plus a great gayborhood (aka Boystown) means there’s lots to do.
GETTING THERE — I took my favorite airline, Southwest, which serves close in Midway Airport. From there you can hop on the Orange Line to your hotel. It’s a quicker ride than from O’Hare although American and United both have hubs there. To get around the city, you can ride the CTA. Get a Ventra card for ease of riding on both it and the “L” (aka the Elevated which is their Metro). They have a great elevated subway system as well as a good bus system. Rental car and Uber not needed.
WHERE TO STAY — I always stay in the Lakeview East neighborhood. Bargain hunters will love The Inn at Lincoln Park (innlp.com or reservations at innlip.com) which has super low weekday rates and reasonable weekend rates. My other favorite is the Hotel Versey which is a music-themed hotel that is also reasonable and is a short walk to Boystown, the gay Village where everyone is welcome.