No matter what your trip to Chicago entails, where you stay always adds a lot to the experience. Looking for Chicago history? Want to stay at the digs with the best hotel bar? Or maybe you have a secret addiction to The Apprentice and are hoping to meet the master behind the hair. Check out our guide below and you will find exactly what you’re looking for (whatever that may be), complete with soft pillows and a turn-down service.

Drake Hotel
140 East Walton Place Chicago, IL
www.thedrakehotel.com
This 10 floor hotel first opened its doors on New Year’s Eve 1920, and the hotels famous red lit Drake sign still shines over the Gold Coast neighborhood. At the Drake you will find one of the most loved restaurants and politician bars in Chicago, and the design of the old architecture is impeccable. No matter if you are staying the night in one of the many individually designed rooms (including a 5 room presidential suite) or just coming to grab a drink at the famous Coq d’Or, you will be treated like the royalty that has stayed there before you.

The Palmer House
17 East Monroe Street Chicago, IL
www.palmerhousehiltonhotel.com
Palmer House opened in 1872, now making it the nation’s oldest continually operating hotel. The history behind this hotel is pretty interesting as well. Thirteen days after The Palmer House began, the great Chicago Fire struck and sadly this hotel took a brunt of it. After reopening in 1873, it continues this day to be a beautiful part of Chicago times past. The hotel hosts a multitude of travelers each year, and many weddings take place here in the Grand Ballroom. Stop by for afternoon tea, which is served in the lobby every afternoon from 2-4, or sip a martini in the lobby bar.

Trump International Hotel
401 North Wabash Avenue Chicago, IL
www.trumpchicagohotel.com
This 92 floor hotel is indeed Chicago’s finest. The design inside and out is flawless, and the rooms even have TVs in the bathroom mirrors. No matter what floor your digs may be on, the view will be amazing, either of the beautiful skyline or the Chicago River. Not to mention the services offered at the 23,000 square foot spa that are some of the best you will find in the city. Even if you can’t quite swing the cash for a room at the Trump, it’s a must to stop by for some tasty cocktails at Rebar, on the mezzanine level. Sink into soft plush chairs overlooking the river and sip away.

The W Hotel
644 North Lakeshore Drive Chicago, IL
www.whotelsofchicago.com
Chicago’s only hotel overlooking Lake Michigan, The W Hotel is flawlessness to the eye. And it’s pretty sweet that from the W you can walk right to Navy Pier or to the Mecca of shopping and dining on the Mag Mile. But no need to even leave the hotel if you do stay here- there’s a fitness center, a spa, an amazing restaurant, and a panoramic view from Whiskey Sky, the cocktail lounge on the top floor.

Hotel Monaco
225 North Wabash Avenue Chicago, IL
www.monaco-chicago.com
This boutique Chicago hotel is rated one of the 40 best hotels in the country, and for good reason. Besides being pet-friendly, another thing that sets this Chicago hotel apart is that the spa services are brought to you right in your room. If your feet are weary from walking the city, no need to go anywhere, they will bring the massage to you. After your pampering head to the lobby for the nightly
complimentary wine hour, and indulge your other senses.

The Wit
201 North State Street Chicago, IL
www.thewithotel.com
Some people do it- and then some people, like the designers behind The Wit Hotel- do it better. The Wit hotel is colorful and stunning from the time you step foot into the artsy lobby until you are sinking into the brightly colored couch in your guest room. Since The Wit is voted as the best hotel bars in Chicago, you have no choice but to take part in some heavy drinking. Check out the 2nd floor Phoenix Lounge for live music and fruity spiked drinks, or head upstairs to ROOF for some cocktails and a kickin’ view at the bar- there’s even telescopes. ROOF was rated one of the “10 best rooftop bars in the country”, go see for yourself. You see? Some people just do it better.

Hard Rock Hotel Chicago
230 North Michigan Avenue Chicago, IL
www.hardrockhotelchicago.com
This 40 floor musically inspired hotel is in the heart of the city, and celebrities and musicians alike are known to bed down here when they come to the windy city. So, no matter if you are a rock star or a groupie, the rooms are polished, and the service is perfection. What makes this hotel seriously cool among most downtown hotels is that it is pet friendly- they even have free pet cams that you can set up in your room and be able to see what Fido is up to while you’re out on the town. Angels & Kings, one of Chicago’s kick ass nightclubs, just moved from their downtown location into the Hard Rock Hotel, so entertainment isn’t a far walk from your rented front door.

The Allerton Hotel
701 North Michigan Ave Chicago, IL
www.theallertonhotel.com
The Allerton Hotel is located in the middle of the Chicago Loop, and the perfect hotel if you’re traveling for business. The entire hotel is equipped for Wifi, including The M Avenue Lounge in the lobby, where emailing over a few cocktails is highly encouraged.

Hotel Felix
111 West Huron Street Chicago, IL
www.hotelfelixchicago.com
What sets this hotel apart from the rest is that it’s eco-friendly, so as you indulge there’s no reason to feel guilty. Just to name a few things that the hotel does to aid in serving the environment are motion detecting heat and air conditioning throughout, energy saving lighting, the carpeting in the rooms is made of recycled materials, and the cups and wipes in the fitness center are reusable. Dining options at the hotel are yummy too. Elate Restaurant has a changing seasonal menu, with many of the offerings being completely local and organic. The bar area has great cocktails and wines, and live jazz is heard here on the weekends.