A great hotel:
The James (Downtown). Sleek modern decor, steps from Michigan Avenue and within walking distance from other downtown attractions, like the Museum of Contemporary Art and Millennium Park. Environmentally friendly options include a "bike package" to explore the city with two Paul Frank road bikes--and the option to offset the carbon emissions from your stay. Bonus: You'll also find amazing Kiehl's beauty products in the bathroom!
Three lovely shops:
Eskell (Wicker Park). You'll find gorgeous clothing and accessories, including the shop's eponymous line, hard-to-find designers, charm necklaces and vintage dresses.
Art Effect (Lincoln Park). The best place to buy a birthday or hostess gift, this shop features beautiful and quirky home goods, clothing and stationery.
Greer (Old Town). Gorgeous and unusual paper goods by distinctive designers. We especially love their illustrated journals and note cards.
Two delicious restaurants:
Southport Grocery (Lakeview). This cafe is famous for its cupcakes and is the perfect spot for brunch. I recommend the "Grown-Up Pop Tart," filled with warm berry preserves, Mascarpone cheese and roasted vanilla walnuts. Yum.
Tango Sur (Lakeview). Unbelievable Argentinian food made affordable by its BYOB policy with no corkage fee. A great restaurant for large groups (and steak lovers!). It's not uncommon to see the sidewalk outside packed with people drinking wine while waiting for a table.
Two fun activities:
Chicago Outdoor Film Festival Grant Park: Every Tuesday from June to August, you can pack a picnic, watch a classic film in the park, and take in the views...Lake Michigan is to your right and the sparkling city skyline is to your left.
The Signature Room: After shopping and sightseeing on Michigan Avenue, head up to the Signature Room on the 95th floor of the John Hancock Center for birds-eye views of the city. (Hint: Skip the Sears Tower--the Signature Room provides a similar experience with no fee to see the view. Plus, you can order cocktails!)
Don't be bashful about asking directions. Midwesterners (even city dwellers!) are laid-back and approachable.