Fly From Chicago To Denver At The Last Minute For Only $338 Round Trip
So it turns out that those dreams of running away into the mountains can be attained for really not that much money. Need a break? Just go west. Take flight and find yourself in the Mile High City, a rapidly development metropolis with that spectacular skyline shadowed by the ridges of the Rockies. And the pricetag for a spontaneous jaunt through the mountains of Colorado, at least transport-wise hovers somewhere about $338.
Pay Over Time No Interest No Fees No Catch
We make it easy to pay your way. All you need to do is pay a small deposit to lock your place on the trip, then you can pay the rest in as many installments as you like. Want to pay monthly installments? Or in 3 big chunks? Its completely up to you. All you have to do is pay in full at least 60 days before your trip departs. Easy.
Fly From Chicago To Boston On A Whim For Only $332 Round Trip
One of the oldest, historically rich, diverse and influential cities in the country, Boston gets an average of 16.3 million visitors a year. There are certainly the baseball hungry pilgrims on route to Fenway Park the history buffs happy to wander the city’s wide variety of top-shelf museums and not to mention those travelling foodies after some fresh seafood and local brews. If you fall under any of those categories and feel like taking off right around now, it’s actually not an expensive trip. For just a bit over $332, last minute deals can come pretty easily for those departing from O’Hare.
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Getaways From Chicago Illinois: The Steamboat House
The Steamboat House is a short block away from Main Street in Galena and offers easy access to shops, restaurants, wineries, and more.
There are five guestrooms with private baths, fireplaces, fine linens, LCD televisions, and DVD players. Room decorations vary with some featuring four-poster beds, original hardwood floors, sleigh beds, and private porches. Guests can enjoy the billiard room, library with games, books, and movies, wraparound front porch, screened garden gazebo, or cozy parlor.
There is wine every evening with hot beverages at night. In the morning, cocoa, tea, and coffee are delivered outside your door and a three-course breakfast is included. Guests can also add various packages that include in-room massages, birthday cake, wine, flowers, chocolate, and/or visits to local wineries. If you are looking for cheap weekend getaways from Chicago, rooms start at $115 per night.
605 S. Prospect St., Galena IL, 800-717-2317
Can I Cancel My Last

Cancellation, like booking, traditionally has to be done well in advance, but Expedia understands that unforeseen circumstances can call for more last-minute decisions. That’s why we strive to offer flexibility in all our bookings, because where you book matters, even if it’s for rentals that are in high demand like Panama City Beach hotels. Many available hotel deals come with free cancellation even with last-minute booking.
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Hawk Valley Retreat & Cottages
Hawk Valley Retreat & Cottages is only eight miles from downtown Galena and has ten acres of secluded gardens and meadows to explore. There are four private cottages and three rooms within the main house. The main house rooms have private entrances, private baths, satellite TVs with DVD players, and wireless internet. All cottages have whirlpool tubs, Wi-Fi, air conditioning, TVs with DVD players, full baths, electric fireplaces, king-size beds, sitting areas, eating areas, kitchenettes, and private porches. One of them also has a separate bedroom.
The ten acres of land include a gazebo, a pond, walking trails, and porch swings. The main house has central air conditioning, a living room, a dining room, large picture windows, and a wrap-around deck. Main house stays come with a complimentary breakfast, and guests have access to home baked cookies, tea, coffee, and water. Rooms start at $90 per night, cottages from $195. Things to Do in Galena
2752 W. Cording Rd., Galena IL, 888-777-6016
How Can You Book A Vacation With Travelpirates
Were always posting new deals, so the easiest way to stay informed about the latest deals for your region is by signing up for our email newsletter by downloading the TravelPirates app. You can also follow us on Facebook, Instagram, and Twitter.
You can also browse through our site to find deals for specific destinations, or types of vacationslike beach vacations, action-packed city trips, or adventurous hiking excursions. If you have a more specific vision of your ideal trip, you can use our search & book tool to filter deals that fit your needs. Simply enter your outgoing airport and your dream destination, pick your dates and number of travelers, and look through the available deals to find the one thats perfect for you.
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Fly From Chicago To Minneapolis At The Last Minute For $228 Round Trip
The flight from Chicago to Minneapolis typically isn’t too expensive, with good deals on average hovering around $99, but thankfully even last-minute trip planners don’t have to worry about missing out on low prices. With average fares only going for $228 when booked the day before travel, Chicagoans can quickly find themselves chilling lakeside with a beer in the Twin Cities without breaking the bank.
Weekend Getaways From Chicago: The Abbey Resort
The Abbey Resort is a full service getaway on 90 scenic acres near the Fontana harbor, offering 334 deluxe guestrooms, 13 spacious suites and 13 villas. The 35,000-square-foot Avani Spa offers massages, facials, wraps, aromatherapy and saunas on your weekend trip.
Resort facilities include a fitness center, aerobic studio, indoor and outdoor swimming pools, a disk golf course, and a games arcade for kids. Dining options range from casual cafes to gourmet restaurants, including 240 West, Café Latte, the Waterfront Restaurant Bar & Grill, Bar West and Porto. Weekend activities include watersports, bike rides, golf, walking and jogging around the lake. If you are looking for affordable resorts near Chicago, rooms start at $89 per night.
269 Fontana Blvd, Fontana-On-Geneva Lake, WI 53125
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Weekend Getaways Near Chicago: The Newport Resort
The Newport Resort is a family friendly getaway in Door County, just minutes from the beach. The resort has 59 rooms and suites with whirlpool tubs, cozy sitting areas and kitchenettes. There is an indoor swimming pool, fitness center, and game room. Guests can read in the library, unwind in the lobby lounge, and stroll through the garden. Located within walking distance of numerous eating establishments in
Egg Harbor, the Newport Resort is a great choice for family vacations and romantic retreats. Sandy beaches, world-class golf courses, and state parks offer plenty of outdoor entertainment during the summer, and cross-counting skiing, snowshoeing, and sledding in the winter. Rooms start at $79 per night.
7888 Church St, Egg Harbor, WI 54209
Expert opinion: Where should I go this weekend for fun? FL, CA, Myrtle Beach, OR, New England weekend, Charlotte, Williamsburg, LA, PA
The Knickerbocker On The Lake
The Knickerbocker on the Lake is a restored boutique hotel located in the heart of downtown Milwaukee. The property is within walking distance of a number of restaurants, museums, theaters, and transportation options. The 160 guest rooms and suites are decorated with period-influenced furniture and modern conveniences such as fully equipped kitchenettes and Wi-Fi. Some suites have views of the picturesque Lake Michigan shoreline.
The full service Knick Salon and Spa offes invigorating treatments, while the Juneau Room is a spacious area ideal for hosting special events. Guests can work out at the 24-hour fitness center, request custom tailoring and valet dry cleaning.The Knick Restaurant offers upscale dining, with a menu that provides something to suit every gourmand. Weekend guests should not miss the bountiful Sunday brunche. If you are looking for cheap weekend getaways, rooms start at just $119 per night.
1028 E Juneau Ave, Milwaukee, WI 53202
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Weekend Getaways Near Me: Mansion Hill Inn
Located in downtown Madison, Wisconsin, the Mansion Hill Inn is a historic getaway with luxurious guest rooms featuring Frette linens, high-definition flat screen televisions, rain fall showers, and Aveda bath products. If you are planning a romantic getaway, ask for one of the suites with whirlpool baths, in-room gas fireplaces, and access to balconies or verandas with a view. Take advantage of the Pre-Arrival Concierge to customize your stay at the Mansion Hill Inn.
424 N Pinckney St, Madison, WI 53703, 608-255-0172
Fly From Chicago To San Juan Puerto Rico With Little Notice For Only $427 Round Trip

How about a spontaneous weekend in the tropics with your significant other? Is an anniversary or birthday coming up that you were originally going to spend on take-out sushi and a bottle of Veuve? Has she been having a rough time lately? Are you in the doghouse for something you did or didn’t do? Whatever the reason, have no fear, since a last-minute return fare to beautiful San Juan comes in at around $427 when booked the day before travel.
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Fly From Chicago To Myrtle Beach At The Last Minute For $233 Round Trip
Are you flailing around the Windy City, wishing you were on a beach? Forget the crowded, over-hip strips of California or Miami sand and instead head to a casual, small-town surrounded by charming Southern seafood restaurants, outlet shops, and of course, excellent beaches. Check Myrtle Beach and marvel at how the return flight only costs $233 when booked the day before flying.
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Getaways From Chicago Illinois: Vrooman Mansion
The Vrooman Mansion is a historic bed and breakfast right in Bloomington/Normal. The historic estate offers luxury and privacy with easy access to attractions, restaurants, and shops. The majority of the decorations in the spacious guest rooms are antique period furniture, with each room featuring its own theme. The suites have down pillows, soft fluffy towels, high-quality linens, microfiber robes, and free Wi-Fi. There are five suites and rooms in the Mansion and two in the carriage house.
The numerous common areas include the Safe Room, the Library, the Foyer, the Music Room, the Dining Room, and the Parlor. Throughout the day, you can enjoy bottled water, soft drinks, and snacks and a full gourmet breakfast is included in every stay. Breakfast features tea, coffee, or cocoa, juice, fruit, and a hot entrée. Rates start at $110 per night.
701 East Taylor St., Bloomington IL, 309-828-8816
Featured Last Minute Vacations From Chicago
Last minute vacations from Chicago dont have to cost you a bundle from savings of up to 60% on things like last minute cruises and even family vacations, you can always find a great deal with Traveloni. After all, just because its a spontaneous getaway doesnt mean you should have to book a room with a delightful view of the parking lot and highway for a high price! When you book with us, all you have to do is pack a couple bags and head to a Chicago airport, well take care of the rest. From finding you great deals on airfare and resort packages, well be here through every step of the way.
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Galena Log Cabin Getaway
Galena Log Cabin Getaway covers 45 acres of secluded land as well as the Adventure Creek Alpaca and Labradoodle Farm. This working farm has 12 log cabins, each with one room and over 660 square feet plus an open loft. There is a modern bathroom featuring a six-foot double-whirlpool tub and large skylight. Cabins have a queen bed downstairs with a double bed in the loft, satellite TV, a fridge, a microwave, and a gas log fireplace. Other amenities include DVD players, central air and heat, and platform rockers. Four of the cabins are dog-friendly.
While at this inn, you can visit or enjoy the alpaca farm, and even take an alpaca for a walk. They also breed Goldendoodles, which guests can spend time with. Guests can hike 1.5 miles along the Adventure Creek or head to Casper Bluff or along the Mississippi River. There is very little light pollution in the area, which means gorgeous views of the stars on clear nights. Rates start at $189 per night.
9401 W. Hart John Rd., Galena IL, 815-777-4200
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The Mansion Bed And Breakfast
The Mansion Bed and Breakfast is located 35 miles to the west of Chicago and gives you the chance to relax on a private estate built in 1907 on your weekend trip. You will find breathtaking stained glass windows, original lighting, and exquisite woodwork throughout the rooms and common areas. Every room has wireless internet, a cable TV with a VCR, premium pillow top mattresses, Egyptian cotton sheets, an iron with ironing board, a hair dryer, and a desk. There are extended stay options available. Some rooms also have two-person whirlpools, private baths, private terraces, and electric fireplaces for added romance.
Guests have access to the extensive video library, board games, and magazines. There are snacks and tea available during the day. A spa, numerous restaurants, and bike trails are just a few minutes away, many of which are within walking distance. Rates start at $139 per night.
305 Oregon Ave., West Dundee, IL, 847-426-7777
Everything You Need To Know About All

What are some of the benefits of booking an all-inclusive vacation?
From the moment you book your all-inclusive vacation package you can kick back knowing everything from your room to your cocktail choice is covered in your one-off fee. Indulge in a bounty of local and international foods, try new activities, and put away your purse on the ultimate stress-free vacation.
How can I find an all-inclusive vacation for adults only?
Use the all inclusive filter, then look for hotels listed as adults only. Many adults only resorts are also all-inclusive, like Excellence Punta Cana – Adults Only All Inclusive on a stretch of private soft sand, with a swim-up bar. Narrow your choice further by choosing amenities like gym or spa and discover places like the gorgeous Valentin Imperial Riviera Maya All Inclusive – Adults Only resort, which has a stunning spa on palm lined shores.
Are there all-inclusive vacation spots in the US?
Yes, enjoy a US all-inclusive vacation where no passport is needed. From ski resorts and city breaks to the beaches of Florida and islands of Hawaiifind your perfect vacation from an abundance of impressive all-inclusive packages in the USA.
What are some of the best destinations for cheap all-inclusive vacations?
Do all-inclusive vacations include airfare?
How can I find the best deals on all-inclusive vacations?
What are some of the best destinations for an all-inclusive Caribbean vacation?
Why should I book an all-inclusive package with Expedia?
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Resorts Near Me: Farmers Guest House
Farmers Guest House is located in historic downtown Galena, giving guests easy access to nearby attractions. Each of the nine rooms and suites is tastefully decorated, providing an intimate setting perfect for couples. All rooms have flat-screen TVs with Blu-Ray/DVD players to watch movies from the inns collection and there is Wi-Fi throughout the property. Other room amenities include private baths, luxurious bath amenities, individual outlets, irons, hairdryers, and plenty of outlets.
The common areas include the Spa Studio, private gardens, and numerous patios. In the morning, guests enjoy a full breakfast with a signature entrée, homemade pastries or bread, fruit, juice, and homemade granola. There is also Wine time every evening with cheese and wine, as well as fresh cookies at night. Guests have access to soda, tea, coffee, and bottled water. Rooms start at $179 per night.
344 Spring St., Galena IL, 815-777-3456
Working For Our Guests Our Communities And The Environment
There are more reasons than great value and a selection of top-class destinations to choose WestJet for last minute flights from Chicago. Our fleet of aircraft is one of the youngest among North American airlines, which means you’ll be able to enjoy a journey that’s comfortable, quiet and above all minimizes the impact on the environment. We’re also proud to continually invest in the communities we serve. WestJetters are able to donate time and energy to the causes they care about thanks to the WestJetters Caring for Our Community initiative, while WestJet Cares for Kids is a program with eight leading charities that aims to improve levels of health and well-being for kids and their families. It all plays into our long-term vision focusing on guest experience, environment-conscious practices and sound corporate culture. Arrange your travel from Chicago through WestJet and you’ll soon see how we’re making a real difference.
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