Arriving in Chicago from Midway or O'Hare? Free parking eliminates nightly fees that often add $30-$60 to a hotel bill. Options here range from basic motels near the airport to the exceptional Ray's Bucktown Bed and Breakfast (guest score: 95), which includes a sauna and complimentary breakfast. For active travelers, The Hotel & Athletic Club at Midtown provides full club access with two pools, tennis courts, and a spa, plus free parking-a rare perk in a major city.
Budget-friendly stays like the Carlton Inn Midway offer a complimentary airport shuttle and breakfast, while the Chicago South Loop Hotel places you minutes from McCormick Place with a spa bath in each room. Most properties cluster around Midway, Lincolnwood, and neighborhoods like Bucktown and Old Town. Expect free WiFi, air conditioning, and often a 24-hour front desk. Family rooms are available at several locations. Reserve early, as these hotels fill fast.