There are plenty of cool things to do/see in both Chicago and Boston, but what you should check out will vary greatly based on what interests you. I've got limited Chicago experience, so I'll leave that for others, but I've lived in Boston for a while and have some general guidance: - Public transit is quite prevalent and lets you get most anywhere in the city. You can and should pick up a weekly combo pass (bus and subway) when you arrive as that will definitely save you money getting around. There are plenty of things to do right off the subway lines, but if you're willing to use buses you can get around to many more places much more quickly. The transit website is http://www.mbta.com and has good general info, but if you've got a smartphone with you you should also grab the "CatchTheBus" app (available for both iOS and Android) as it has live times for service at almost all bus and subway stops. - Tons of great museums of all stripes (many are closed or have limited hours on Monday, so check websites). On the Green Line of the subway you can get to the Museum of Fine Arts (classic huge museum, lots of early archaeological collections, medieval - early modern Europe, early America), the Isabella Stewart Gardner Museum is an absolutely brilliant collection of all sorts of things displayed as they were in her jaw-dropping home (This is how it is to be of the Hyperelite/Socialite backgrounds) that I find far more fascinating than the MFA. If you take the Red Line over the river into Cambridge there are several great museums at Harvard, including the Natural History Museum with some truly incredible botanical and taxidermy collections (one of the best in the world, actually), the Peabody anthropological museum, and several smaller art museums in and around the Harvard campus. There are also many beautiful buildings and lots of great dining, shopping and strolling about in the immediate area. If you head down towards the harbor (several subway lines, or Silver Line bus service) you can hit the Institute of Contemporary Art, which is a very dynamic institution. I haven't been down for the current exhibitions, but the main event is one on street art featuring work by Los Gemeos from Brazil. It's right on the water, so there's plenty of good walking to be had, and a variety of great seafood immediately available. Also, a truly fantastic clothing store, Louis of Boston, is a short walk away, and they have a lovely restaurant as well. - Newbury St./Boylston St. has all sorts of shopping and dining, several historic churches and great architecture, and runs down towards Boston Common in the Back Bay area (about in the center of things, you'll be going back and forth through there several times on your visit). You can easily kill a day just wandering around there. - If you're interested in American revolutionary history you can start wandering around the Common and pick up one of many tours for the Freedom Trail, and there are a number of small graveyards, historic buildings, small museums and the like that are scattered from there to the harbor. - If you want to poke around and relax on a nice day you might want to check out a Boston harbor cruise that either goes out on a specific circuit, or hop on one of the ferries (also through the MBTA website linked above - spend some time checking things out there) to go around to the parks and walking trails on the small islands. - I have faith in your ability to find bars and clubs, but if you're looking for a specific type let me know. If you enjoy alcohol, though, you owe it to yourself to check out descriptions of bars carefully as there is an embarassing overabundance of bars with phenomenal beer selection and some stunningly good craft cocktail skill. The Sunset in Allston (student area past Boston University, on the B Green Line) has more than 100 different beers on tap and about 300 or so bottles to choose from. Drink is one of the best for cocktails. Cheers.