Downtown Chicago Vacations
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Where to stay in Downtown Chicago
Magnificent Mile
Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.
The Loop
Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.
River North
Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.
Lincoln Park
Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.
West Loop
Consider a visit to The Old Post Office and take some time to enjoy the abundant dining options during your time in West Loop. If you want to see more of the city, jump on the metro at Racine Station or Ogilvie Transportation Center.
Discover the most popular places to visit in Downtown Chicago
Downtown Chicago Hotel Deals
Hilton Vacation Club Hotel Blake Chicago
Hilton Vacation Club Hotel Blake Chicago"Every thing is good!👍🌹"
DoubleTree by Hilton Chicago - Magnificent Mile
DoubleTree by Hilton Chicago - Magnificent Mile"The room was dirty, the curtains had some brownish spots that looked like blood, the restroom was not clean at all. And there is some weird smell inside the rooms, i will hive a 0 stars if i could."
Hampton Inn & Suites Chicago Downtown
Hampton Inn & Suites Chicago Downtown"Okay location, close to public transportation. Excellent subway system. Bus system okay. Walkable to numerous sights and river is nearby. Nordstrom and Macy's nearby if you're looking for better shopping. Variety of restaurants within walking distance, though most were just casual eating eateries. Seems to be many bars nearby. Airport is half hour subway ride, Amtrak a short Lyft away. The hotel was comfortable and clean, the room was large enough for the two of us. But the lighting...
LondonHouse Chicago, Curio Collection by Hilton
LondonHouse Chicago, Curio Collection by Hilton"Upon arrival we were greeted immediately. The staff helped us unload our bags into a luggage cart and valet took the car to park. Our room was available for early check in. We stayed in the 7th floor in a single king room. Everything was clean and the views were great. We went up to the 22nd floor to see the river views from the rooftop bar. This hotel is in an absolute perfect location to see Chicago. You are close enough to walk to river walk, millennium park, the train, and magnificent mile....
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
Hotel Saint Clair- Magnificent Mile
Hotel Saint Clair- Magnificent Mile"Clean Hotel, but Disappointing Customer Service I’ve stayed at this hotel multiple times while traveling to Chicago for classes. While the hotel is clean and conveniently located, the inconsistent customer service has been disappointing. During an earlier stay, I asked for bottled water and was directed to paid vending machines. Later, I noticed other guests receiving complimentary water at check-in. When I asked during subsequent stays, I received it too. While minor, this reflects the...
La Quinta Inn & Suites by Wyndham Chicago Downtown
La Quinta Inn & Suites by Wyndham Chicago Downtown"1500 characters are not enough to describe the roach motel feel and the attitude given for wanting to not be disgusted by the room you were assigned. Wasn't expecting fancy, but did expect clean and functional.. 2 expectations that apparently were set too high. Walking on the bathroom floor sounded like velcro being pulled apart from your shoes sticking to the tile. The shower drain looked like a chia pet with human hair. The carpet was disgusting, and their solution apparently was to...
Frequently Asked Questions
How much does a Downtown Chicago vacation package cost?
Go from looking to booking with our Downtown Chicago vacation packages, which start from just . Handpick the hotels and flights that suit your travel style. Then, add on a couple of tours or activities for an amazing adventure.
How do I get a cheap travel package to Downtown Chicago?
Bundle your bookings with Expedia to save big on your next trip. With more than 550 partner airlines and 1,000,000 hotels across the world, your Downtown Chicago vacation package can be tailored exactly to suit your budget. With all that extra money, why not include one or two fun tours and activities? It's an easy way to unlock even more savings. The vacation you've always dreamed of in Downtown Chicago is much closer than you thought!
How far in advance should I book my Downtown Chicago vacation?
While not all airlines advertise tickets early, you can normally look up international airfares on Expedia up to 12 months in advance. This is the time you'll score some incredible deals. If you've left things to the last minute, you could still be in luck. Discounted prices occasionally emerge a few weeks before departure.
What does an Expedia Downtown Chicago travel package include?
Packages include flights, hotels and rental cars, but you can mix and match them to create your ideal Downtown Chicago trip. You can also add on fun things like activities and tours once you've made your booking. You're in charge! When you combine your bookings with Expedia, you'll score discounts you won't find elsewhere.
What should I know before booking a Downtown Chicago travel package?
Our prices are always low. However, you'll pick up even better deals if you book your hotels, flights and car rentals together. With an Expedia travel package, you'll get transparent pricing and tons of choice.
Can I choose my airline with a Downtown Chicago Expedia vacation package?
Yes — that's the beauty of an Expedia vacation package. You're in charge! We have more than 550 partner airlines throughout the world, so you have lots of choice when arranging your Downtown Chicago trip.
If I'm not able to travel, can I cancel my Downtown Chicago vacation package?
You can. We understand that even the best-laid plans can go awry, so we're happy to help if you have to make changes to your Downtown Chicago vacation package. You may be able to change or cancel your itinerary for free if you've booked in the last 24 hours. Your airline, hotel or car rental company may impose a fee if your booking was made more than 24 hours ago. Have a look at our Customer Service Portal for further information. Also, be sure to check your itinerary for the finer details on change fees.