Downtown has a plethora of hotel options. It consistently has more of the best rated hotels than any other city in North America. The problem is that they are not cheap, all of them usually cost over $300 a night and often cost much more. There are a lot of good options in the $200-$300 range. There are a few upscale places in the $125-$200 range. To spend less you will have to stay out away from the tourist attractions and sights. Hotel rates do vary greatly with the seasons and from week to week. Rates can be lower in the winter after the New Year and before spring break. If you drive be careful of the parking rates which can be up to $40 a night. The City of Chicago garage under Millennium Park offers better rates than any of the inns. The are some inexpensive centrally located hotel options in downtown Chicago.
Most of what you will want to see is in a pretty compact area downtown. Staying anywhere in the Gold Coast, Magnificent Mile, River North or Loop will leave you with a walk or short cab ride to most of the best sights and attractions. The Loop can be a kind of deserted at night but it also offers the best value on weekends.
Chicago's hotels are very competitive and the prices vary from month to month and from day to day. Your best option is to pick your price range and area where you want to stay and go to a hotel booking site.
The Best of the High End Hotels:
The Ritz-Carlton: Situated on the Magnifiencent Mile. It has all of the glitz you would expect from Ritz-Carlton. It has a high-end restaurant. Top notch service has the ability to handle almost any request.
The Four Seasons: Everything that applies to the Ritz also applies to The Four Season. They are run by the same company so that is not surprising. I would recommend going with whichever one has the best deal. Try to get a room on a higher floor for the best view of the lake.
The Peninsula: A new entry into the high end market. More urban and hip than the other top of the line Chicago hotels. It is in a great spot on the Magnificent Mile. Has a sophisticated pool with a small sun terrace overlooking the city. The Shanghai Terrace is one of the most upscale Asian restaurants in Chicago. Pierre Gourmet offers simpler fare in a relaxed setting and is one of our favorite places to go to get a simple lunch.
Trump International Hotel & Tower: I am not a fan of Donald Trump, and the hotel, it's restaurant and lounge try too hard to be hip and more effort seems to placed on looks and appearances than substance. But it has a lot of pluses. It is ideally situated on the Chicago River just a block off of the Mag Mile. It is right in the middle of everything but it is in a quiet area. It has amazing views down the waterway, of the city and even the lake. The rooms are very large, well equipped, and modern.
The Drake: Every city seems to have a stately, old hotel that is the city standard for luxury. The Drake is Chicago's version. At the end of Michigan Avenue on the lakefront. It has a classic, old time luxury hotel lobby and it is the place to go for the city's best afternoon tea.
The Hyatt: On a central spot, a short walk from the Mag Mile, Navy Pier and Millennium Park. Try to get a room facing the water for better views. The Hyatt is a very large hotel with a huge lobby, so it does lack intimacy and sophistication. It has an open air lobby lounge with great views. Usually one of the best deals for someone looking to stay at a very good but not high end hotel.
The Wit: Probably the hippest hotel in Chicago. The lobby is a parade of the young and good looking on weekends. The rooftop lounge is a see and be seen place in the summer. Good rates are often available on weekends. It can be downright cheap on select weekends.
Sofitel: In the Gold Coast in a somewhat quieter, more residential area. Surrounded by Gold Coast restaurants and stores. Sophisticated but not stuffy. It has a highly rated restaurant and the lounge is a good place for a quiet drink.
Palmer House: Downtown in the loop it is close to Millennium Park, the Art Institute of Chicago and most other attractions. It is a short cab or bus ride from N. Mich. Avenue. It is one of Chicago's oldest and most important hotels. A recent renovations has restored its charm and sophistication.
Public: Formerly known as The Ambassador. In Chicago's most exclusive neighborhood. In a quiet area, near taverns and restaurants but a bit out of the way for walking to other attractions. It is where Hollywood elites stayed on their way across the country years ago. The restaurant was a hangout for numerous stars and is still a good place for a quite, romantic dinner. Was the home of Harry Caray for years.
The Intercontinental: On the Mag. Mile it is one of the cities architectural highlights. It has a good lobby lounge, a wine bar and a restaurant that is a good place to go for lunch. It has one of the best indoor pools in Chicago.
The Blackstone: An historic hotel on S. Michigan. Recently renovated it has resumed it's former glory. The restaurant Mercat a la Planxa located in the Blackstone is the cities best place for tapas. It is a bit south of most tourist destinations but is well located for Millennium Park, the Art Institute, the Field Museum and Shedd Aquarium. East rooms have great views but many of the rooms have limited views. My brother's standard double room on a recent stay was very large and well appointed.
Conrad: A classy hotel with very well appointed rooms. The hotel is trendier than the people who stay there. Set in an ideal spot, on Michigan but with a back entrance that is in a quiet street. The outdoor rooftop lounge is a romantic spot to feel like you are young and hip even if you are not.
W-Lakeshore: A trendy hotel, at least the lobby area. It has a hip vibe but it is not a relaxing place. The rooms are fairly small and the bathrooms are not only small but have sliding doors which do not offer as much privacy as regular doors. The spectacular rooms, their name not mine, have great lake views. It is not as much in the middle of things as most hotels, but it is in a quieter part of the city.
Cheap But Still Nice Hotel Options:
The Allerton: Well situated in the heart of the Mag Mile. It is historic and has recently been renovated. Watch parking because it can wipe out the money you saved by staying here.
Embassy Suites Lakefront: A newer hotel with large rooms that make it ideal for families. It is walking distance from Navy Pier and Michigan Avenue. It is often busy and noisy so it is better for families than for a romantic getaway. Pool.
Radisson Hotel: Well placed, near many of the places you will want to go in Chicago. Recently renovated. It has an English Pub on the ground floor.
Hotel Indigo: Set in the residential neighborhood of the Gold Coast. It is convenient to restaurants and the trendy area of N. Rush Street but is a about a mile from the Mag. Mile. Looks more like an ocean front hotel than a city high rise. Was tastefully redone a few years ago.
Hotel Cass: Completely redone a couple of year ago. It is a good looking hotel with okay rooms that is well situated and sometimes comes with free breakfast. One of the best options for people looking for a reasonable priced room near the all of the things they want to do in Chicago.
Inexpensive Hotel Options in Chicago That Are in a Safe Area To Stay:
Holiday Inn -Merchandise Mart
Red Roof Inn
Best Western River North. It is nothing fancy but it has free parking which can save drivers a lot of money and is near most of the places you will want to go.