Take advantage of an air/hotel deal from Southwest Vacations or hotel packages that emphasize the city's shopping and iconic architecture.
Taste of Chicago, airfare and three nights from $439 per person
Book this air/hotel package from Southwest Airlines Vacations, and you'll receive three nights at the Palmer House Hilton, which earned a Historic Hotels of America designation for preserving its landmark beaux arts architecture and two-story, gold-tinged lobby. Pause on your way in to admire the ceiling's opulent scenes from Greek mythology. You'll also receive round-trip airfare on Southwest and $50 off a two-day or more Go Chicago Card, which covers tours of the city, entrance to museums, and discounted dining. Note that the package is timed to Taste of Chicago, a 10-day annual food festival, held June 27-July 6 this year. Upgrade to the Westin Michigan Avenue for $75.
When: June 26-July 6, 2008.
Book by: June 21.
Gateways: Nashville; add $12 for Columbus; $123 for Birmingham; $140 for Tampa Bay; additional cities available.
Details: Hotel taxes included. Does not include airport taxes and fees of about $32 per person. Package prices are per person for three nights, Thursday or Sunday departures. Use promotion code TASTE50. Based on double occupancy; single supplement is $295.
Contact: 800/423-5683, southwestvacations.com.
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.
For more tips on what to do, visit the Chicago Convention & Tourism Bureau's Web site, 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).