Midwest & Chicago Vacation Packages, Resorts & Hotels

Midwest & Chicago Vacation Packages
$179+

Welcome Inn Manor Bed & Breakfast - Chicago
All-inclusive packages available

Find out why this charming and elegant Bed & Breakfast is the #1 B&B in Chicago on TripAdvisor. Warm and accommodating, a stay in any of the 7 unique rooms will be one to remember. Take advantage of their All-Inclusive package by April 30 and receive food, transportation and drop off services all in the price of your 3-night or more stay. Enjoy daily breakfast, chef prepared dinner for two one night, and courtesy car service to a Chicago-area destination.


Midwest & Chicago Vacation Packages - Visit Chicago, Branson & the Dells

The midwestern states of the U.S. provide the vacation destinations of Chicago, Detroit, St. Louis, musical Branson, the waterparks of Wisconsin Dells and historic Mackinac Island where cars are not permitted. For more excitement, visit the rollercoaster capital of the world at Cedar Point near Sandusky, Ohio. Whatever your interest, here are some midwest and Chicago vacation packages to help you plan.

Midwest & Chicago Vacation Packages
$151+
Baker's Sunset Bay Resort -Wisconsin Dells
  • Free Kalahari theme park tickets
  • Lakeside, free kayaks & rowboats
  • Pools, nightly bonfires, pet-friendly
Midwest & Chicago Vacation Packages
$5+
Discounted Car Rentals Nationwide
  • Choose from top brands
  • Availability at 75+ major airports
  • Economy, luxury, SUV, compact & more
Midwest & Chicago Vacation Packages
$90+
The Beach House - Mackinaw City, Michigan
  • Charming little lakefront cottages
  • BBQ grills, kitchenettes, free wi-fi
  • Heated indoor pool & spa, pets accepted
Midwest & Chicago Vacation Packages
$212+
Hampton Inn & Suites Sandusky / Milan, OH
  • 10 miles to Cedar Point and Lake Erie
  • Free hot breakfast or grab-n-go bags
  • Free wi-fi, cribs, gym, heated pool
Midwest & Chicago Vacation Packages
$209+
Drury Plaza Hotel St. Louis at the Arch
  • Near the Arch, zoo, museum, & more
  • Free hot breakfast, wi-fi, popcorn daily
  • Pet friendly, 24-hr gym, indoor pool
Midwest & Chicago Vacation Packages
$175+
Warwick Allerton-Chicago - Magnificent Mile
  • Recent multi-million dollar renovation
  • Luxury bedding, docking station, minibar
  • Walk to many attractions & events
Midwest & Chicago Vacation Packages
$131+
Treehouse Condominiums - Branson
  • Special $99/nite til 5/24, call for info
  • Lakeside, view of Table Rock Lake, pool
  • Minutes from Branson shows & activities


Tour the Windy City with Our Chicago Vacation Packages

Looking for fun Midwest vacations for your family? Look no further than our affordable Chicago vacation packages. Join the more than 50 million visitors who come to Chicago each year for tourism and vacations.

Chicago is packed to the brim with entertainment options. If you’re a fan of shopping, peruse the Magnificent Mile, Navy Pier, and State Street shopping areas to get a few upscale gifts for friends back home. You can also grab a bite to eat at one of the city’s highly-ranked restaurants, or even take a walking tour of the city’s architecture. Though the city is ranked the sixth most walkable in the United States, you can rest your tired feet by taking a ride on the famous L train that loops through the city above the streets.

Due to the tragic Great Chicago Fire, a huge building boom took place in the late 19th and early 20th century, creating one of the densest and tallest skylines in the world. There are many notable structures that combine innovation and experimentation, including the Aqua building, 35 East Wacker, the Chicago Board of Trade Building, the Chicago Cultural Center, and the Chicago Water Tower. It’s also home to some of the world’s tallest buildings, including the Willis Tower and the Trump International Hotel and Tower. Many Chicago tours can lead you through the streets while explaining the history and significance of these buildings.

One of the highlights of Chicago is Grant Park, which sits comfortably on the eastern side of Lake Michigan and offers spectacular views. Within this park is the famous Millennium Park, which is a 24.5-acre area that was created to celebrate the coming of the second millennium. In the park, you can gaze at the reflective Cloud Gate or admire the picturesque Crown Fountain.

For sports fans, stopping at Wrigley Field is a must. From there, you can spend the rest of your day watching animals at the Lincoln Park Zoo, learning new knowledge at the Museum of Science and Industry, or catching a performance by the Chicago Symphony Orchestra. The best way to see all of these sights is to choose one of our Chicago vacation packages, which will keep you organized and help you find a great Chicago hotel to stay in.

Winter Park Colorado

Search Vacations

Travel more and spend less with Dunhill Travel Deals - your source for the best travel deals, with exclusive specials, sales and discounts
on travel to top destinations worldwide. With Dunhill Travel Deals, save up to 70% on hotels, cruises, vacations, airfare & more!