Maybe you've forgotten how expansive Chicago really is. Maybe you need to revisit the city as if you were a tourist to remember what makes it so great. Maybe you just have friends in from out-of-town and you really don't want to spend a mint on taking them out.

Start out with a Free Trolley Tour, which runs from 10 a.m. to 6 p.m. on weekends. For the best overview of the city, hop on the Red Trolley Line, which runs on a loop that includes State Street, the Sears Tower, the Chicago River and the Lyric Opera House. Get off where you started and head over to the 95th floor of the John Hancock building. The Signature Lounge at 95th offers a panoramic view of Chicago and Lake Michigan. The 21-ounce Signature Punch, a delicious concoction of Bacardi light and dark rum with fruit juice, costs $9.25. Other cocktails cost about $8-$10, but soft drinks are only $5. Try and snag a seat by the window and watch for the L, as it looks like a Lionel train from this height. Ladies, make sure you stop in the women's room and take your female guests with you—it offers the best view in the place, if not the city.

Total cost: Depends on what you're drinking, but a half-hour trolley tour, amazing view and one drink shouldn't run you more than $12 with tip.