Illinois Vacations, Resorts, Rentals, Suites and Getaways

Chicago rises from the shores of Lake Michigan with its instantly recognizable sky-scrapped silhouette. Amusing rides, fun fare, shopping, and stunning cityscape views have made Navy Pier one of the most popular destinations in all of the Midwest. Millennium Park melds arts, cultural programs, concerts, and family activities in a town square of truly epic proportions. But, a trip to the Windy City is certainly not complete without a shopping trip to the famed flagships stores that line “The Magnificent Mile.” Rich tradition and diversity is also witnessed in the city’s flair for all things culinary. World famous pizza, top chefs, and cuisine from seemingly every corner of the globe all have a spot at the table Chicago sets. Expand your world with a trip to the Windy City. 

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Lakefront BeachesLakefront Beaches
Lincoln Park ZooLincoln Park Zoo
Navy PierNavy Pier
Shedd AquariumShedd Aquarium
Wrigley FieldWrigley Field
Where To Stay

Wyndham Grand Chicago Riverfront

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71 East Wacker Drive, Chicago, IL

Chicago goes by many names: the Windy City, the Second City, the City of Broad Shoulders, or just affectionately “Chi-Town.” But whatever you call it, you can call it home at Wyndham Grand Chicago Riverfront. Set against the Chicago River, just steps from the famed cultural district simp...

Once upon a time, Galena, Illinois was a classic boomtown, rich in the shining mineral for which it was named. These days, the mines are closed--but Galena is still a hidden gem.  With 85% of the town acting as a historic district, Galena is dedicated to preserving as much of the city's nineteenth century architecture as possible.  This has led to Galena being recognized as one of the most beautiful places to visit in the U.S., as well as one of the country's most stunning small towns.  A popular destination for vacation-goers craving a piece of the past, Galena is the perfectly place to go horseback riding and sightseeing.  And if you're feeling adventurous, you might even want to try a ghost tour.

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Popular Family AttractionsView All
Ulysses S. Grant HouseUlysses S. Grant House
Chestnut Mountain ResortChestnut Mountain Resort
Thunderbay FallsThunderbay Falls
Blaum Bros Distilling Co.Blaum Bros Distilling Co.
Galena on the FlyGalena on the Fly
Where To Stay

Wyndham Galena

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5129 West Longhollow Road, Galena, Illinois

Tucked away in the beautiful woodlands of Illinois, the Wyndham Galena combines peace and quiet with Midwestern creature comforts and historic charm.  Eight miles away from downtown Galena, the resort offers a chance to get away from it all, with outdoor activities all year 'round.  During...

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What Our Travelers Are Saying
Sep 01, 2019
I absolutely love that I found Tripbound to book with. I have used them to stay at the beautiful Wyndham-Bonnet-Creek in Orlando for my Disney trips and I don't think that I will ever be able to stay at a Disney resort again. I am spoiled by the location and luxury of this resort. Knowing that I can book through Tripbound and save money seals the deal for me. I also enjoy that I can make partial payments to book my trips. They are super easy and friendly to work with.
terri z
Apr 21, 2019
Very Helpful and informative, they answered every question I had and was very patient with me while I tried different places. They also found me a better deal than I was expecting. I will use them again!.
Mrs M
Aug 13, 2018
Awesome experience!! Team Tripbound made planning our family's summer vacation easier than expected. There were no hangups; our room/accomodations were as described and check- in at the resort was "pressure-free" (i.e, timeshare sales). I'd give 10 stars if I could. Team Tripbound is highly recommended by me & mine!
David C
Apr 27, 2018
Been using Vrbo, homeaway, and numerous others for approx 20 years. Never had such personal involvement like Tripbound. Best ever!!!