Package Deals from Chicago to Key West from $2481

Located in Key West, Florida, this motel is just 7 minutes’ walk from the Southernmost Point of the United States. It features rooms with free WiFi access. Air conditioning is available in each room at Seashell Motel for hot Florida days. Rooms are simply decorated, and guests can take advantage of a 24-hour shared kitchen. Bicycle rentals are available at the Seashell Motel Key West. Daily maid service and vending machines are provided for added guest convenience. The property offers free parking. Duval Street is a 15 minutes' walk from the Seashell Motel. Higgs Beach is a 10 minutes' walk away. Guests will be just a 3 minutes’ drive from the Ernest Hemingway Home and Museum. Please note, as part of our commitment to enhance our property and services, we are currently in the process of room and property renovations. The construction work will take place from 8:00 AM to 5:00 PM, every day from Monday to Friday, with no construction activity happening on weekends (Saturday and Sunday).

Beachside Resort & Residences Hotel features a private sun beach and a pool with Gulf of Mexico views. Guests can enjoy a meal at the on-site restaurant or grab a handmade cocktail at the poolside bar. A free shuttle to Key West city center is provided. All accommodations at the Key West Beachside include a flat-screen TVs with bluetooth TV speaker. A refrigerator is offered in all rooms. Select rooms feature upgraded amenities such as a full kitchen, balcony, and spa bath. A living area and dining area are also offered in select rooms. Guests may work out at the water view fitness center or soak in the outdoor hot tub. Nearby activities include the Key West Golf Club, biking and jogging trails, and several water sports. Private indoor parking with Private garage parking service is available on site. Tavern N Town ever-changing dishes include steak house favorites and seafood delicacies. The Chicken Walk Poolside Bar offers casual meals, light snacks and tropical cocktails. Key West Airport is less than 1.2 mi away.

Offering an outdoor pool, this historic Key West property is just 1 minutes’ walk from Duval Street. Free WiFi and a light continental breakfast are provided daily to all guests. All air-conditioned rooms include a cable TV and private bathroom. Cottages include a full kitchen and seating area. A pool view is included with select units at Courtney's Place Historic Cottages and Inns. Guests can grill a meal at the barbecue facilities. This Key West Courtney's Place Historic Cottages and Inns provides free on-site parking as well. The shops and restaurants of Mallory Square are 15 minutes’ walk away. Guests can also cool off at Smathers Beach 1.9 mi from the property.

Great care is taken to ensure guests experience comfort through top-notch services and amenities.Stay connected with your associates, as complimentary Wi-Fi is available during your entire visit. The hotel offers taxi and shuttle amenities for your ease in navigating around Key West (FL). When arriving by car, take advantage of the hotel's convenient on-site parking facilities. The hotel offers reception amenities including concierge service, express check-in or check-out and luggage storage to ensure a comfortable stay for guests. Should you require assistance, the ticket service and tours can also aid in booking tickets and securing reservations at the finest shows and events in the vicinity. Whether you're here for an extended stay or simply require fresh garments, the hotel ensures your cherished travel attire remains spotless and accessible with the convenience of dry cleaning service located on the premises. The hotel's daily housekeeping ensures an excellent option for your stay.Need something at the last minute? The convenience stores has you covered, ensuring your requirements are met without any inconvenience. To ensure the well-being and convenience of all visitors, smoking is strictly prohibited throughout the entire hotel. Smoking is permitted solely in the specified smoking zones allocated by hotel.In order to ensure the utmost level of relaxation, the guestrooms feature an inviting design and are equipped with all basic necessities, creating a delightful stay experience.To ensure a pleasant stay, a selection of rooms at hotel come furnished with linen service, blackout curtains and air conditioning, all designed with your ease in mind. Several chosen accommodations at Blue Flamingo Resort Key West have a separate living room incorporated into the room design. In select rooms, visitors can enjoy a touch of amusement with the availability of television and cable TV for their entertainment needs. Within specific rooms, a refrigerator, a coffee or tea maker, bottled water, instant tea and mini bar is conveniently available for your use. Understanding the significance of bathroom facilities in enhancing visitor contentment, hotel offers a hair dryer and toiletries within a few chosen chambers. How about kicking off each day of your getaway with a delicious cup of coffee? At the hotel, relish in the invigorating taste of a freshly brewed, excellent coffee. Various excellent meal offerings at hotel ensure that enticing and easily accessible options are constantly available. Upon your arrival, don't miss experiencing bar for enjoyable in-house evening entertainment. Throughout the day, engage in the entertaining activities available at Blue Flamingo Resort Key West.Unwind by the pool at hotel and cherish a leisurely moment. Enjoy a refreshing beverage al fresco at hotel's poolside bar savoring your preferred concoction. Guests who enjoy maintaining their fitness regimen while on holiday can visit the fitness center provided by hotel.

Offering 2 outdoor pools, this Old Town Key West motel features high-speed WiFi access and a cable TV in each room. Duval Street is 2 minutes' walk away. All rooms include a microwave, refrigerator, hair dryers, and plush eurotop mattresses. Extras include daily continental breakfast, convenient bicycle on-site, beach access, and our Tipsy Rooster Bar and Liquor Store. A concierge desk and luggage storage are available at Southwinds Motel. Parking is available on-site. Laundry facilities is also at the property. The Ernest Hemingway Home and Museum is 12 minutes' walk away. Guests at the property can rent bicycles to explore the area. Fort Zachary Taylor Historic State Park is less than 2 mi away.

Located off Duval Street, this bed and breakfast is just 2 minutes' walk from The Ernest Hemingway Home and Museum. A breakfast is served daily. Each room at the Seascape Tropical Inn have a small refrigerator and a flat-screen cable TV. Rooms are also equipped with a ceiling fan, air conditioning, and private bathroom. Guests of the Key West Seascape Tropical Inn can relax on the 2 sun terraces or in the tropical garden. Free WiFi is provided to all guests. The deluxe continental breakfast includes champagne mimosas, waffles and fresh bagels. Guests can enjoy their food on the breakfast sun terrace. Fort Zachary Taylor Beach is less than 1 mile from the property. The SouthernMost Point of Continental USA is 10 minutes' walk away.

Paradise Inn - Adult Exclusive is located in Key West and features landscaped grounds with brick paths and a lotus pond with koi and tropical turtles. A complimentary continental breakfast is served in the lobby. The suites at Paradise Inn - Adult Exclusive include a sitting area with cable TV. A microwave, refrigerator, and coffee facilities are furnished in each accommodations. Free WiFi is provided. Enjoy complimentary wine and cheese hour on site at Paradise Inn - Adult Exclusive. Additional amenities include an outdoor pool with a fountain feature and an outdoor hot tub. The hotel is happy to arrange sightseeing tours. Higgs Beach and the Key West Aquarium are 5 minutes' drive from Paradise Inn - Adult Exclusive. The Key West Museum-Art & History is a 15-minute walk away.

Silver Palms Inn, located in historic Key West, has an outdoor pool and is a 9-minute walk from the Ernest Hemingway Museum. Guest rooms offer private balconies and 40-inch flat-screen TVs. Complimentary continental breakfast is provided. Rooms at Silver Palms overlook the pool or city and have microwaves and refrigerators. Guests also have access to Wi-Fi, a desk and lounge chair in their rooms. Suites have an island view and sofa bed. Silver Palms has covered parking. A continental breakfast is also available to guests. The Harry S. Truman Little White House is less than one mile from Silver Palms Inn. Fort Zachary Taylor Historic State Park is 1.4 miles away.

Hampton Inn Key West features a heated pool with an ocean view. Guests can grab a bite to eat at the poolside restaurant. A free buffet breakfast is offered daily. Complimentary WiFi is provided. Shuttle service to Key West Airport is provided to all guests. Duval Street is 4 mi from the property. These resort rooms are completely nonsmoking and include a microwave and a small refrigerator. A cable TV with HBO® and local art are featured in each room. Select rooms feature a balcony. Convenient laundry facilities are offered. A business center is available for guests. The resort provides a 24-hour multilingual front desk. Cheekie Hut is a poolside bar and grill that serves American cuisine. Guests can also grab a hot beverage at the coffee bar. The Hemingway House is a 13-minute drive from the property. Please note guests must be at least 21 years of age to check-in or accompanied by a parent or legal guardian. Please note all room rates at this hotel are based on 2 guests. Additional charges apply for further guests.

Located just 1 mile from historic Duval Street, this Key West hotel features a heated swimming pool and a daily continental breakfast. Free WiFi is available throughout the property. A flat-screen TV with cable channels are available in each room at The Palms Hotel. A ceiling fan and telephone are included. Select rooms offer a seating area and kichenette. A picnic area and barbecue are accessible as well. Bicycle rentals are offered. The daily continental breakfast is served poolside and includes pastries, juices, and fresh fruit. The Southernmost Point is just 1.1 miles from this hotel. Guests will be 9 minutes’ drive from Key West International Airport.

This bed and breakfast welcomes guests to Old Town, Key West and features a free continental breakfast, 3 outdoor pools and a hot tub. The Ernest Hemingway Home and Museum is 15 minutes’ walk away. Free WiFi access and a flat-screen cable TV are provided in each room at this Key West NYAH - Adult Exclusive bed and breakfast. Guests can stroll through the garden or ask the tour desk for area recommendations. The 24-hour reception offers luggage storage. The nightlife, shops, and art galleries of Duval Street are 9 minutes’ walk from the property. Key West Aquarium and Key West Cruise Port are each 0.7 mi away.

Coco Plum Inn is located in the heart of Key West, Florida. Guests can start their day with a made-to-order breakfast and then take a dip in the heated outdoor pool. Complimentary WiFi is provided for all guests. Smathers Beach is 2.8 mi away. Rooms feature a TV with cable channels. A refrigerator, coffee maker, and microwave are provided as well. Guests will enjoy the comfort of a furnished seating area. Select rooms feature a balcony and spa bath. This adult-only bed and breakfast includes a garden and concierge service. A packed to-go breakfast and bicycle rentals are available. The bed and breakfast is 1050 feet from Hemingway House and 2100 feet from Key West Aquarium.

This historic Key West Orchid Key Inn - Adults Only is on Duval Street 3 minutes’ walk from the Ernest Hemingway House and Museum. Features include a daily continental breakfast, heated pool with a hot tub, and a bar. A 42-inch flat-screen cable TV, microwave, and small refrigerator as well as an iPod dock are standard in each room. Extras include a Keurig® coffee machine, and some suites have a spa bath and a sofa bed. A Complementary single welcome drink voucher upon check in. The Orchid Bar serves specialty cocktails made with fresh herbs and infused spirits from early afternoon to late evening. Guests will receive 1 complimentary beverage per day. The inn is 3 minutes’ walk from the Historic Lighthouse and 7 minutes’ walk from the Southernmost Point. Key West city center is 1 mi away.

Located above a nightclub on historic Duval Street in Key West, Florida, this gay male guest house features an outdoor swimming pool, a clothing-optional sundeck, and an on-site restaurant. A daily continental breakfast is available, as is daily complimentary happy hour. A microwave, refrigerator and coffee-making facilities come standard in each room at New Orleans House. A flat-screen cable TV is included. Free Wi-Fi and a fitness center are accessible at the Key West New Orleans House. Other facilities include luggage storage and laundry facilities. The property is located above Bourbon Street Pub. The Southernmost Point is just 10 minutes’ walk from this guest house. Guests will be 4 minutes’ walk from The Ernest Hemingway Home and Museum.

This Art Deco hotel in downtown Key West has a large pool-side sun terrace and rooms with a flat-screen TV. All guest rooms at Pegasus International Hotel are equipped with free Wi-Fi. A refrigerator and microwave are provided. A year-round heated pool and a hot tub are part of this Key West hotel, and towels are included. The front desk is open 24 hours a day and laundry facilities are available. The Pegasus International Hotel is 6 blocks from the Key West Aquarium. The Ernest Hemingway Home and Museum is 3 blocks away, and Smathers Beach is 3 miles from the hotel.

Nestled along the Florida Bay, a short drive from historic Old Town Key West, Florida, this property offers an outdoor pool, casual cafe and a variety of activities. Parrot Key Hotel & Villas is surrounded by lush landscaping and gardens. Guests can go for a swim in one of the 4 outdoor pools, then enjoy a snack from the poolside The Grove Kitchen & Bar. The property is completely nonsmoking. Guests at the Parrot Key Hotel & Villas can spend the day kayaking. After a kayaking trip, guests can relax with an on-site massage or take the complimentary shuttle to the historic Key West old town city center. A 55-inch flat-screen TV and small fridge are featured in each accommodations at the Parrot Key Hotel & Villas. Guests can relax on their private terrace and enjoy views of the ocean and tropical landscape. For only $30 + tax per vehicle per night, enjoy 24-hour unlimited in and out valet service. PLEASE NOTE, THIS IS THE ONLY OPTION FOR PARKING (No self-park parking or street parking available in the area)

Lighthouse Hotel is located in the heart of iconic Key West, opposite the Ernest Hemingway Home and Museum and the Keeper's Quarters Museum. Guests can enjoy an outdoor heated pool, complimentary continental breakfast, and on-site bar. Isabel's Poolside Bar serves island favorites and specialty drinks. Guests can explore the area by renting one of the bicycles from a specialized company. Free WiFi and a flat-screen cable TV are included in all accommodations at Lighthouse Hotel. A private bathroom is also provided in each guestroom. Duval Street is 5 minutes' walk from the hotel, and the Southernmost Point is 7 minutes’ walk away. Guests will also be 8 minutes' walk from Key West Butterfly and Nature Conservatory.

Offering an outdoor pool, Duval Inn is located in Key West. Free WiFi access is available. This Key West bed and breakfast includes both an indoor and outdoor seating area as well as a refrigerator. The private bathroom includes free toiletries. Beds are outfitted with linens. Learn about the life and times of writer Ernest Hemingway at Ernest Hemingway Home and Museum (1640 ft) or view the sights and venues of Duval Street (328 ft). Mallory Dock is located 12 minutes' walk away.

Located in Key West, Florida, this adult-only hotel offers two outdoor pools. Duval Street is a 1-minute walk away, and Key West Butterfly and Nature Conservatory is 3 minutes’ drive from the hotel. A private balcony or patio with property views is provided in all rooms at The Gardens Hotel Key West. A flat-screen cable TV, ironing facilities, and a refrigerator are also featured in each room. Free Wi-Fi is available for guests. Guests can also take advantage of on-site bicycle hires, massage services, and concierge services. Live jazz music is performed in the gardens every Sunday evening as well for guests to enjoy. The Key West Shipwreck Museum, Key West Aquarium, and Conch Tour Train are all located less than 1.2 mi away. The Ernest Hemingway Home and Museum is 1640 ft away from The Gardens Hotel.

Located along Duval Street in Old Town Key West, Florida, this historic hotel offers modern amenities such as free wireless high-speed internet access and an on-site restaurant. La Concha Key West, Autograph Collection features an outdoor pool, Pool Bar, and contemporary fitness center. Mater sports (within 2 miles) and same day Dry Cleaning available. The guestrooms at the La Concha Key West, Autograph Collection boast unique services for a memorable stay. Guests can enjoy a 55-inch flat-screen TV. After a busy day, the pillow-top mattress offers a restful night's sleep. The restaurant at La Concha, Perla, offers unique, island-inspired small plates and fresh local seafood. The historic Duval Street is also home to a variety of fine dining, nightclubs, and more.

Facing the beachfront, Ibis Bay Resort offers 3-star accommodations in Key West and features an outdoor swimming pool, garden and private beach area. Among the facilities of this property are a restaurant, a 24-hour front desk and a concierge service, along with free WiFi. Private parking is available on site. At the resort, every room is equipped with a closet. Complete with a private bathroom equipped with a shower and free toiletries, guest rooms at Ibis Bay Resort have a flat-screen TV and air conditioning, and selected rooms include a terrace. All rooms will provide guests with a fridge. The area is popular for cycling, and bike rental is available at the accommodation. Ernest Hemingway Home and Museum is 2.5 miles from Ibis Bay Resort, while Duval Street is 2.5 miles away. Key West International Airport is 1.2 miles from the property.

Offering an outdoor pool and a restaurant, Havana Cabana at Key West. is located in Key West. WiFi access is available, and the shops and restaurants of Mallory Square are 14 minutes’ drive. A 42-inch flat-screen TV with high-definition channels, a refrigerator, and a coffee machine are provided in all rooms. Extras include an en suite with free toiletries as well as a desk and blackout drapes. Set amid lush landscaping and featuring a rock waterfall, the pool at Havana Cabana at Key West. offers a spacious seating area for sunbathing. An on-site hot tub is nestled nearby. Duval Street is 15 minutes’ drive while Key West International Airport is 5 minutes’ drive.

This adults-only bed and breakfast is within a 10-minute walk of Duval Street and the Atlantic Ocean. The environmentally-friendly inn provides in-room refrigerators, bike rentals and a continental breakfast. Every room at The Grand features local Caribbean artwork and private entrances. In-room media includes an iPod docking station, free Wi-Fi and flat screen cable TVs. The Ernest Hemingway Museum is a 15-minute walk from the Guesthouse. The Butterfly and Nature Conservatory is a 10-minute walk from the hotel. Parking is free and available, both on site and on the street.

This Hyatt Windward Pointe is located in Key West, 3.5 mi from the Southernmost Point, and features a year-round outdoor pool and hot tub. A fully equipped kitchen is provided in every apartment. Additional en suite amenities include a private bathroom, balcony and ironing facilities. A separate living room is also included. Enjoy the on-site barbecue facilities at Hyatt Vacation Club at Windward Pointe. Bicycle hires are available, and fishing, scuba diving and parasailing are available nearby. Southernmost Point is 3.1 mi from Hyatt Windward Pointe, while Duval Street is 3.1 mi away. The nearest airport is Key West International Airport, 0.6 mi from the property.

Located in Key West's Old Town, this beachfront The Reach Key West, Curio Collection by Hilton features a 137-yard private beach and rooms with a private balcony. Duvall Street is 15 minutes' walk away. A refrigerator and flat-screen TV are standard in each room. The Reach Key West, Curio Collection by Hilton also includes an en suite and bathrobes. Some suites and studios have a sofa bed. An outdoor pool is on site and the full-service Spa al Mare at an adjacent sister property, Casa Marina, is available to guests. The Key West Golf Club is 5 mi away. On-site activities, including scuba diving, snorkeling, deep-sea fishing and kayaking. Earnest Hemingway Museum is just 10 minutes' walk from the The Reach Key West, Curio Collection by Hilton.

Boasting panoramic water views, Oceans Edge Key West, Preferred Hotels & Resorts Collection offers 6 swimming pools and a waterfront bar and restaurant. Complimentary WiFi is provided for all guests. Duval Street is 19 minutes' drive from Oceans Edge Key West, Preferred Hotels & Resorts Collection. Guest accommodations feature views of the water and include a balcony or patio. The private bathroom comes stocked with free toiletries and a hairdryer. A flat screen TV is provided in all rooms. Suites feature additional living space. Select rooms feature an additional bathroom. The hotel includes a paddle shop, onsite water sports, and a 165-slip marina. Yellowfin Bar and Grills specializes in American-Caribbean creations. Southernmost Point is 5 mi from the property. The nearest airport is Key West International Airport, 1.9 mi from the property.

This boutique hotel is just 10 minutes’ walk from Duval Street and Key West's nightlife and dining options. It offers a daily continental breakfast. Guests can enjoy the on-site outdoor pool. Museums, water-sports and shopping are located within walking distance of the property. The Southernmost Point of the USA is 1 mile away. Mallory Square and the Key West Aquarium are also less than 7 minutes' walk away.

Ideally set on a private beach in Key West's Old Town, Pier House Resort & Spa offers a full-service spa, instant beach access, and on-site dining. It is 1 minutes’ walk from Duval Street entertainment district. WiFi is complimentary, and every guest room features a small refrigerator, rain-style showers, and coffee and tea-making facilities. A flat-screen TV comes standard. Experience waterfront views from the outdoor pool or stay indoors and relax with massages and body rituals at the on-site spa. For added wellness, visit the on-site fitness center. Savor fresh seafood and classic dishes for breakfast, lunch and dinner at the One Duval or sample cocktails near the seaside at Beach Bar. Two additional restaurants are on-site, including quirky Chart Room Bar. Nearby, adventure awaits via boat, parasailing, or Jet Ski. Hemingway Home and Museum is 5 minutes’ drive from Pier House Resort & Spa.

This all-suite hotel in Key West is only 1 block from the Atlantic Ocean and Duval Street. Each suite is equipped with a full kitchen and 48-inch flat-screen cable TVs. Two outdoor heated pools are surrounded by gardens at Santa Maria Suites Resort. A full-service concierge. Smoothies and fresh fruit are served poolside and guests can also enjoy a complimentary daily happy hour featuring wine and hummus. Free WiFi is available in each suite at the Santa Maria Resort. Washers and dryers are included. The Clinton Market Square shopping area is a 5-minute drive from the resort. The Ernest Hemingway House is an 11-minute walk away and Fort Zachery Taylor Historic State Park is 1.3 miles away. All rooms receive fresh baked muffins, Dove ice cream mini bars and chocolate sweet treats delivered daily to your suite.

Lobby Renovations through February, 2026. Valued guests - We are excited to be redesigning our main entrance and adding a stunning new lobby with a bar and lounge that will overlook our marina. Work will be completed Monday to Saturday 8:30AM to 6:00PM. Our Restaurant, Spa, Pool and Sunset Pier will be operating as normal. Overlooking the Gulf of Mexico, this luxury Key West resort and spa features an outdoor pool with gulf views. Free WiFi is provided at Ocean Key Resort and Spa. On-site SpaTerre offers massage therapies, nail treatments, facials, and other spa services. The resort houses an on-site fitness center and fishing boats, jet skis, and glass-bottom boat tours are available. From spa baths and private balconies offering partial and full ocean views, rooms and suites at Ocean Key Resort come well equipped. A coffee machine and a private bathroom are also featured. Enjoy dinner and dancing over the water at Sunset Pier or experience seafood paired with crafted cocktails at waterfront Hot Tin Roof. LIQUID Pool – Bar - Lounge serves cocktails and snacks. Mallory Square plaza is 1 minutes’ walk as are the restaurants, bars, and entertainment of Duval Street.