Safe bet Americana on Michigan Avenue would seem to put Bandera right in your crosshairs. It's not especially Chicago--I think it's part of a restaurant group based in California. It is, however, one floor off the street, and the tables along the window provide some of the best views of Michigan Avenue you'll find outside of Spiaggia (most definitely NOT a shorts and tennies place). The menu is primarily beef, chicken, lamb and ribs roasted over wood fire with Southern-ish sides including cole slaw, corn bread, fries and mashed potatoes. It's about as unadventurous as restaurants get, but I think their
chicken sandwich is preternaturally good.
[Warning: Cheeseball Touristy Recommendation Ahead] Sitting outside at Cheesecake Factory is a nice way to enjoy the relative serenity of the Hancock Building Garden Level while keeping a close eye on the thrumming throngs at street level.
For something out of the ordinary, Oak Street Beachstro is the only actual beach-based full service restaurant in the city (Castaways not included). For that privilege, along with great views and people-watching, you'll pay a premium for middle-of-the road contemporary fare.
For a cheaper Oak Street Beach option, pack a picnic basket at L'Appetito, an excellent Italian deli in the same Hancock Garden level concourse as Cheesecake Factory. You'll need to eat earlier, since it closes at 6:30. The cold beef sub is spectacular and the panini are various and good. I've grown unreasonably attached to their three bean salad, which carries a harsh bite of raw onion with every forkful and swims in far too much olive oil. For the less sadistic, there are another dozen pre-made salads to choose from, a large sandwich board, fresh pizza, arancini, packaged higher-end Italian foodstuffs, six or so flavors of gelato, good Illy coffeee and great bakery items for dessert.
Have fun!
Bandera
535 N. Michigan Ave.
312-644-3524
Oak Street Beachstro
1001 N. Lake Shore Drive
312-915-4100
L'appetito
875 N. Michigan Ave.
312-337-0691