Downtown Chicago Hotel Guide for First Time Visitors

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According to the Chicago Tribune, 58 million people visited Chicago in 2018 – a record-breaking number for this city.  Conde Nast’s Traveller magazine voted Chicago ” the number one big city.”

But why should Chicago be on the bucket list for the woman over 50 traveling by herself?  Here are my reasons:

  • Culture, food, the arts – you name it, Chicago has it all.
  • Excellent public transportation, making it easy to get around
  • 6th most walkable city in the US
  • Did I mention the great tasting food?

A woman on her own will have amazing choices for hotels in this beautiful city.  But, oh my God, there are so many downtown Chicago hotels to choose from!

In this article, I will be discussing the best hotels to stay in a while visiting downtown Chicago.  I have categorized each hotel by price and location.

Many of the hotels mentioned, I have had the pleasure of staying in or have gotten great recommendations by friends and family.

Clicking on a link in this article will lead you to, which is my favorite booking site for hotels.

  • $$$$ – Luxury
  • $$$ – Moderate
  • $$ – Budget

What you need to know about downtown Chicago

I’ve chopped up Chicago into little sections or hubs of hotness.  These areas are where you will have the absolute best time ever and will be in close vicinity to a lot of stuff.

  • The Loop (including South Loop and West Loop)
  • Wacker Drive
  • River North/Magnificent Mile
  • Streeterville
  • Gold Coast

Each downtown Chicago area has its unique character and charm.  Each hub of hotness has incredible choices when it comes to the best hotels in Chicago downtown.

Chicago Loop

Hotels located on Michigan Avenue in the Loop are the best places to stay due to their proximity to downtown Chicago attractions.  Most of the hotels along Michigan Avenue offer magnificent views of the city and Lake Michigan.


$$$- $$$$  Chicago Hilton (720 South Michigan Ave)

The Chicago Hilton is one of a few hotels downtown Chicago whose rooms offer unobstructed views of Lake Michigan.  The Chicago Hilton’s luxury style has been updated over time but has managed to stay true to its old-school charm.  For more information on the Chicago Hilton, click here.


$$$$ – Chicago Palmer House (17 East Monroe Street)

The Palmer House is another historic Chicago luxury hotel that you must experience at least once in your life.  What I love about the Palmer House is once you step inside this grand hotel, you leave the noise, hustle, and bustle of city life behind and step into noiseless opulence circa the 1920s.

On exhausting days I would hang out in the Palmer House‘s huge-ass Parlor/Bar with a martini, and people watch. Did I mention that it is also a Hilton property and just like its sister hotel, the Chicago Hilton, is a member of the Historic Hotels of America?  One of many famous Chicago hotels in the downtown area.

The Palmer House is located near:

  • State Street shopping
  • Art Institute of Chicago
  • Millennium Park
  • Theater District
Palmer House, courtesy of

$$$ – Hampton Inn Majestic (22 West Monroe)

The Hampton Inn Majestic is located in Chicago’s Theater District.  Right next door to the Majestic is CIBC Theater.  It is located one block away from shopping on State Street.  Rooms range from 285 square feet to 350 square feet.  Click here for more information.

Nearest areas of interest:

  • State Street Shopping
  • Italian Village Restaurants
  • Block 37
  • Theater District
chicago hotel guide
Hampton Inn Majestic, courtesy of

$$$-$$ – Central Loop Hotel  (111 West Adams)  

The Central Loop Hotel is located in the heart of the business district.  What does that mean?  Amazing bars with impressive cocktail happy hours are within walking distance of this hotel and a chance to hobnob with the business crowd looking to toss a few back before heading home.  Quite impressive if you’re into people-watching.

The Central Loop Hotel is within walking distance of:


chicago hotel guide
Central Loop Hotel, courtesy of

$$ -$ – Congress Plaza Hotel (520 South Michigan)

Step outside this hotel, and you’re in the “thick” of it.  Traffic, both vehicular and pedestrian, is insane. Still, you’ll be crazy close to the many festivals (Lollapalooza, Taste of Chicago, to name a few), and running events (Chicago Marathon, Hot Chocolate 5K) held in downtown Chicago.

  • Art Museum of Chicago is a mere 7-minute walk from the Congress Hotel.

chicago hotel guide

Wacker Drive/Riverwalk

I feel that Wacker Drive is so beautiful and lovely in the hotness factor that it deserves to be mentioned in this article!

Wacker Drive follows the Chicago River and creates this curvy crack between the Loop and the rest of downtown north of Wacker. The views are breathtaking, and you’re a short distance away from the Riverwalk.

$$$$ – Radisson Blu Aqua (221 North Columbus Drive)

The Radisson Blue Aqua in Chicago is the first Radisson Blu built in the United States.  The architect for the Aqua is a woman over the age of 50…awesome!  That alone is inspiring enough to book a stay at this beautiful hotel.  The Radisson Blu Aqua is pet-friendly, so bring along your furbabies.  Rooms range from 332 square feet to 1732 square feet.

Nearest points of interest:

  • Millennium Park
  • Chicago Riverwalk


Radisson Blu Aqua, courtesy of


$$$ – Chicago Hyatt (151 East Wacker Drive)

Every time I go inside the Hyatt, I’m petrified that I’ll get lost!  The Chicago Hyatt is its own little city.  A lot of big conferences are held here.  What I love about the Chicago Hyatt is the rooms are very nice, and the hospitality is top-notched. Rooms range from 335 square feet to 2296 square feet.  One of the best hotels to stay in Chicago.

Its location is:

  • one block from the Magnificent Mile
  • steps away from the Riverwalk
Hyatt Chicago, courtesy of


$$-$ – The River Hotel (75 East Wacker Drive)

The River Hotel is located on the south bank of the Chicago River.  The hotel is stylish but not overly expensive for a boutique hotel.  The rooms are small (picture…petite, perfect for the solo traveler), but the location, price, and views of the Chicago River are fantastic.  Click here to check rates.

Location:  Steps away from Chicago Riverwalk

River North/Magnificent Mile

Art meets entrepreneurial ingenuity in River North.  Business is transacted during the day, but at night the River North area lets down its hair from its neat bun and has fun.

This part of Chicago was once filled with factories.  Nowadays, those old factory buildings are artist’s studios and workspace incubators for new businesses.

River North is also known for its vast collection of art galleries on Superior and Huron Streets.  Only New York City has more art galleries.

$$$$ – Langham Chicago (330 North Wabash)

One of four 5-star hotels in Chicago.  The Langham, designed by architect Mies van der Rohe, boasts an understated elegance coupled with a view of Chicago that will take your breath away.  Expect spacious rooms with floor to ceiling windows.  Rooms range from 516 square feet to 2700 square feet.  Click here for rates.

Langham Chicago, courtesy of


$$$ – Residence Inn Chicago Downtown/River North (410 North Dearborn)

One of the best hotels in Chicago downtown for the solo woman traveler over 50 on a budget who wants to save money by cooking her meals. Also, perfect for the multi-generational family who wants to vacation together.  Residence Inn River North offers extended-stay rooms equipped with kitchens.  Room size ranges from the 401 square feet studio suite to the 844 square feet 2-bedroom suite.  Click here for rates.

What’s near the Residence Inn Chicago Downtown River North:

  • Chicago Riverwalk
  • Merchandise Mart
  • Willis Tower (Skydeck)
  • House of Blues
Residence inn river north, courtesy of


$$$ – $$ – Best Western River North (125 West Ohio Street)

The Best Western River North offers the best value for your vacation budget with a location near great eating places such as Rain Forest Cafe, Gino East, and Hard Rock Cafe.  The room has been updated since I last stayed here.  They have a sleek, modern flair that the Best Western brand is now known for. One of the few hotels with an inside pool.  Click here for rates.

Best Western River North, courtesy of


$$$ – Westin Chicago River North (320 North Dearborn St)

A beautiful and relaxing hotel located right on the Chicago River and across the street from the House of Blues Chicago (329 North Dearborn St).  Room size ranges from the 398 square feet traditional room to the 1200 square feet luxury suite.  Click here for rates.

What’s near:

  • Chicago Riverwalk
  • Merchandise Mart
  • Willis Tower (Skydeck)
  • House of Blues
Westin River North, courtesy of


A lot is going on in the near north side downtown neighborhood of Streeterville.  You got Navy Pier to the east and the Magnificent Mile to the west.  Walking this portion of town can be overwhelming with its line of upscale stores and tons of pedestrian traffic.

$$$$ – Ritz-Carlton Chicago (160 East Pearson)

One of four 5-star hotels in Chicago, the Ritz-Carlton is located in the Water Tower Place (shopping mall).  The Ritz is known for its elegance and personalized stays.

Its location near the Magnificent Mile is ideal for the woman looking to get some shopping in a while visiting Chicago.  Rooms range in size from 380 square feet to the 1405 square feet Ambassador Suite.  Click here for rates.

Ritz Carlton Chicago, courtesy of

$$$ – Sheraton Grand Chicago (301 East Water Street)

The Sheraton Grand Chicago, located on the north side of the Chicago River, is a massive hub of activity due to its size and the fact that it is one of the city’s most modern conference facilities.

But that doesn’t mean you won’t be wowed by its hospitality and a fantastic view of the city.  The Sheraton Grand is within walking distance of the Mag Mile, the Riverwalk, and Navy Pier.  Rooms range in size from 332 square feet to 800 square feet.  Click here for rates.

Sheraton Grand Chicago, courtesy of

$$$-$$ – Fairfield Inn and Suites Chicago Downtown/Magnificent Mile (216 East Ontario St)

I love how this hotel meshes well with the surrounding residential neighborhood.  And it’s located a short walking distance from the Mag Mile.  Rooms at the Fairfield Mag Mile have that homey-comfy decor that is very inviting.  Rooms range in size from 205 square feet to 330 square feet.  Click here for rates.

Fairfield Inn Mag Mile, courtesy of

Gold Coast

Just north of downtown Chicago is the Gold Coast and Old Town areas (Near North of downtown) and the neighborhood of Lincoln Park.  These areas north of downtown are considered very hip, very affluent with plenty of fun stuff to do. It is a nice mix of beautiful and historic homes, local businesses, hip restaurants, and shops.

If you choose to stay in hotels in this area off of downtown Chicago, expect to pay expensive downtown Chicago hotel rates.

The Gold Coast/Old Town area and Lincoln Park has plenty of cool things to do in itself that I highly recommend checking out this area of Chicago even if you decide to stay downtown.

$$$ – Claridge House (1244 North Dearborn Pkwy)

The Hotel Indigo is no longer! It has been remodeled and is now known as the Claridge House (1244 North Dearborn Pkwy).  The name has changed, but the charm of this boutique hotel has not. It sits on a residential street amongst beautifully stunning Queen Anne, Romanesque and Georgian Revival-style homes in the Gold Coast neighborhood.  Rates for the Claridge House is amazingly affordable for this part of the city.

where to stay in chicago
Claridge House, courtesy of

Ambassador Chicago

The Ambassador Hotel (1301 North State Pkwy) was legendary for the rich and famous, such as Sammie Davis, Jr, Frank Sinatra, and Marilyn Monroe, that would stay here regularly.  This boutique hotel is still going strong in the 21st century under new ownership. Click here for rates.

where to stay in chicago
Ambassador Hotel, courtesy of

If you get the chance to stay here (rates aren’t bad), explore the little nooks and crannies of this famous hotel that are perfect for chilling out, sipping on a cocktail and reading a book.  The renowned restaurant inside the Ambassador Hotel, the Pump Room is now called Booth One, and I hear the food is still fantastic.  I’m glad the owners kept the Library Bar, which currently serves coffee and fresh pastries; however, the real treat is the charm and beauty of this room – don’t miss stopping by.

where to stay in chicago
The Library, Ambassador Hotel courtesy of


Nearby attractions – Gold Coast/Old Town Area

  • Zanies Comedy Night Club
  • Second City Chicago
  • Oak Street Beach
  • Chicago Lakefront Trail

Where to eat and drink

  • Gibson Restaurant and Bar
  • Tavern of Rush
  • Luxbar
  • Hugo Frog’s Bar and Fish house


Tips on scoring Chicago hotel deals

Hotel prices in downtown Chicago fluctuate depending on the season and what’s going in the city.

Expect downtown Chicago accommodations to fill up quickly during the spring/summer months.  The city is in festival mode, and there’s a lot of conventions in town during these months.  Competition is fierce for hotel rooms.

Before booking accommodations, be sure to check out what is going on in town and plan accordingly.   Hotels prices tend to decrease at the begging of the week and start rising by Friday.

Book well in advance for summer travel to Chicago

* Warning: some hotel chains such as Marriott, Hyatt, and Hilton have more that one hotel location.  Double-check to make sure you’re booking the hotel you want at the location you want.


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