W Chicago-Lakeshore, from $279 per room per night
If shopping is a priority, the Escape to Michigan Avenue package is for you. Stay in the luxe W Chicago-Lakeshore and receive a $50 Magnificent Mile gift certificate per room reservation, valid at any business that's a member of the Greater North Michigan Avenue Association (including the Hard Rock Cafe and H&M). Also included in your package is a 30-minute carriage ride for up to four people (booked at your convenience by the hotel) and two cocktails at Whiskey Sky or the Living Room Bar, two of the W's hot spots. Whiskey Sky even has a panoramic view of the city. Rates begin at $279 per room per night. When Through Sept. 1, 2008. Details Does not include taxes of 15 percent. Use OWT promo code. Double or single occupancy bookings. Contact 312/943-9200, starwoodhotels.com/whotels.

InterContinental Chicago, from $289 per room per night
Calling all architecture buffs: Book the Chicago Architecture Adventure and receive a one-night stay at the InterContinental, a private iPod audio tour of the landmark hotel, and two Chicago architecture tours for two. Choose from the Architecture River Cruise, Downtown Deco, Modern Skyscrapers, and others led by the Chicago Architecture Foundation. A concierge will call you to set up your personal adventure, saving you the time and money (up to $60) of doing it yourself. Rates start at $289 per room per night, or $578 for the two-night minimum stay. When Through Sept. 1, 2008. Details Does not include taxes of 15 percent. Use code Insider City. Double occupancy bookings only. Allow three days advance booking; two-night minimum stay required. Contact 866/210-8811, icchicagohotel.com.

Cloudgate Sculpture at Millenium Park (Justin Lightley/Getty) [enlarge photo]

For more tips on what to do, visit the Chicago Convention & Tourism Bureau's website, which also has a few hotel room deals, including a chance to see the Broadway musical Wicked.

Read these guidelines before you book any Real Deal.

Getting There If you opt for one of the hotel packages, you'll need to book your own transportation. A recent Kayak search for round-trip flights to Chicago in late June yielded fares of $243 from Boston (AirTran), $246 from Miami (American), $299 from New York City (JetBlue), $431 from L.A. (Continental), and $527 from Seattle (Delta).

Related Stories:

• Guidebook Smackdown: Chicago Deep Dish

• Eat Like a Local: Chicago

• Girlfriend Getaways: Chicago Chic

• How to Spend Your Tax Rebate