3.2 miles from downtown
Lincoln Park – historic, conservative and thriving. Home to Ivy League alumni and ladies lovingly referred to as "Trixies," it’s a hubbub of activity day 'n night. Find a foodie scene for any budget (try “Wiener Circle” for Chi-style hot dogs), stroll-worthy Lincoln Park Conservatory for an orchids overload, and shows at the Steppenwolf Theatre.
Places to stay from $25 a night
1.4 miles from downtown
History meets modern chic on the Upper East Side. Come here for a stroll, unless you’re one of the lucky few buying in one of the USA’s most elite zip codes. You’ll see mansions many a style, from Norman Gothic to Tudor. There are plenty of Michelin-star eateries, and the area’s flanked by Lake Michigan and Oak Street (for all your spa and couture needs).
Places to stay from $75 a night
0.8 miles from downtown
The name says it all – Bloomingdale's, Saks Fifth Avenue, Neiman Marcus, Apple’s swanky flagship store, and designer brands galore. Save a buck for the bucket-drumming street musicians, have drinks at the John Hancock Center’s Signature Lounge (95th floor with an endless view)…or crown yourself King or Queen shop-a-lot.
Places to stay from $22 a night
0.2 miles from downtown
Make a loop de loop in The Loop with the many bakers, bankers and vacationers. Downtown is a party day in and day out because it’s home to the city’s best spots. Skip the skyscrapers, but don't miss The Rookery’s "light court" – architect Frank Lloyd Wright’s magnum opus. Dine with the ladies who lunch on Rush Street, or museum-hop ‘til the sun sets.
Places to stay from $58 a night
Near North Side
0.9 miles from downtown
Bam! You’ve discovered the fabled land of fun! Shop ‘til you drop on Magnificent Mile, a street with every store you could possibly imagine. Go on a kid-friendly wander to Navy Pier for fun rides and thrills on the giant Ferris wheel, or just walk around the Water Tower, a historic building that’s a stark contrast to the skyscrapers around it.
Places to stay from $22 a night
Fly by the 9-to-5ers and straight to the Chicago Cultural Center. Visceral, inspirational—look up at the triumphant Tiffany Dome—this building’s visitor center is a great resource for what’s good in the windy city. The Art Institute of Chicago’s elite collection is an essential stop, as is the Magnificent Mile for shopping 'til you drop.
Places to stay from $22 a night
Situated right in the heart of the American Midwest and nicknamed the ‘Windy City’, Chicago is bound to blow you away. From towering skyscrapers offering panoramic views over the vast Lake Michigan to world-famous museums, America’s third-largest city has something for everyone.
In terms of architecture, it’s hard to know where to look first when you’re in Chicago. You can’t miss 875 North Michigan – previously known as the John Hancock Center. At 1,500 feet tall, it looms large over the city and was one of the world’s tallest buildings when it was completed in 1969. Other buildings of note include the neo-Gothic Tribune Tower – which has fragments of the Taj Mahal, the Great Wall of China, Angkor Wat and the Great Pyramids embedded in its exterior – and the Prairie-style Robie House.
The multitude of museums and art galleries found here is arguably the jewel in Chicago’s crown. The big hitters are the Art Institute of Chicago, the Field Museum and the Museum of Science and Industry, but there are others which are well worth a visit. Head to the Adler Planetarium for a chance to see high-tech astronomy exhibits, or explore the vibrant National Museum of Mexican Art.
If lip-smackingly good food and hefty portions is your thing, then you’re going to need to loosen your belt. From deep-dish pizza washed down with lager to spicy beef sandwiches and peanut butter and banana waffles, Chicago is a culinary powerhouse.
From $69 per night
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|Most popular time to visit||October-December|
|Cheapest time to visit||January-March|
|Average weekend price||$206 per night|
|Average weekday price||$219 per night|
|Average stay||2 nights|
I spent five years in early 90's in Chicago and have been back ever since even though each time, I did not stay for long. Mostly for business. Chicago remains to be one of my favorite cities. It, however, has its own problems, especially you have to be careful, very careful where you are and exercise abundant precautions. Some areas simply are off limits. Apparently, the city government has done as much as possible to make the city livable and safe, but they've largely failed so far. The consequence of crime is simply too light, not much of a deterrent and law-abiding citizens could not carry weapons to defend themselves. Of course, day time walking along lake shore is still my favorite thing to do while in the windy city.
Chicago is always amazing. Easy to take CTA (train) Blue Line to Chicago station then take Chicago Street bus to Clark street.. or Take Blue line to Washington and Transfer to Red Line getting off at Chicago station
Chicago is a fantastic tourist destination. there are so many fun things to do. the public transportation is fabulous. the locals are some of the nicest people in the world, ever. great food, museums, fun activities. the weather is great in the summer. the city is clean and easy to navigate. i love it so much in Chicago, i'm moving there.
So much to do for anyone! Museums, shopping, tours, ethnic food of all kinds and good public transportation. It all makes a great city to visit. We loved the Shedd aquarium, the Field Museum and the Art Institute. The Blue Man Group was good and entertaining for all age groups.
Use to be a very beautiful city. I didn't see any police the entire weekend. Roads are unclean. Expressways are untended with overgrowth everywhere. People everywhere talking about all the carjacking. A terrible demise of. once world-class city I loved.
I loved touring the Fredrick Robie House and seeing some of the University of Chicago. Liked going to the Neaderlander Theatre. Loved the food at the Cheesecake Factory, especially, the Cheesecake! We also liked Giordano's Pizza. Having a Starbuck's and Stan's Donuts on the corners was really convenient. We used the Brownline the 1st day to downtown when we should of used the redline and had to walk a few miles in 90° heat. 3 of the 4 of us old ladies were about to pass out. Used Uber the rest of the trip and it was great.
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