An Insider’s Guide to Chicago Downtown Hotels

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where to stay in Chicago

Chicago Downtown Loop Hotels


  • Chicago Hilton – (720 South Michigan Avenue) –   It is one of a few hotels downtown Chicago on Michigan Ave. that 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 without being dated, dusty or faded.  Be sure to check out the pool area and the workout room if you love exercising; you will not be disappointed. One of the top hotels in Chicago.
Chicago Hilton, courtesy of



  • Chicago Palmer House (17 East Monroe Street), is another historic Chicago luxury hotel that you must experience at least once in your life.  What I love about the Palmer House is although this hotel sits in one of the noisiest blocks in downtown Chicago (the L’ runs along the Wabash side of the Palmer House) 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.
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 CIBC Theater (currently playing “Hamilton” <<<< click the link to check prices) and a block away from shopping on State Street.  One of the best hotels, Chicago downtown, for the solo traveler over 50 who wants to be close to the Theater district and my favorite Target store (1 South Street).  Rooms range in size from 285 square feet to 350 square feet.


  • 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 interesting if you’re into people-watching.  The Central Loop Hotel is within walking distance of the Willis Tower, and the Skydeck  <<< click the link to check prices for the Skydeck.

Looking for hotels near Chicago Theater District? Click here to research the best hotel rates.

where to stay in chicago



  • 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 but 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. And if you’re in love with art, the Art Museum of Chicago is a mere 7-minute walk from the Congress Hotel.


Neighborhood Snapshot -The Chicago Loop

where to stay in chicago

What is the Loop in Chicago?  I consider the Loop area of downtown the heart of Chicago.  The Loop got its name from the fact that the elevated trains “loop” around this area of the city.

The Loop area of downtown Chicago includes the business and theater district.  The action settles down after business hours when everyone heads home.  During the day, is the best time to see the Loop in motion.

Hotels in the Loop area that are located along Michigan Avenue are the best places to stay in Chicago’s downtown area.  They offer the best views of the Chicago Lakefront and Lake Michigan.

Michigan Avenue is a hotbed of activity.  If you are looking for peace and quiet stick to the hotels west of Michigan Avenue.

Many Chicago attractions are within walking distance of hotels in downtown Chicago. If you have an opportunity, have a seat at one of the many sidewalk cafes along Michigan Avenue that spring up during the warm months of Chicago and be ready to be wowed.

where to stay in chicago

What to do in the Loop

There are plenty of things to do in the loop area of downtown Chicago.  You will not get bored.  It’s impossible.  My favorite thing to do is to purchase the Chicago Explorer Pass.  It’s a great way to get in a lot of Chicago sightseeing at a nice discount.  The Chicago Explorer Pass allows entry into 3, 4, or 5 attractions or activities such as


For more information on the Chicago Explorer Pass, click here.

where to stay in chicago

Where to eat in the Loop

  • Berghoff Restuarant (17 West Adams Street) Great German food
  • Yolk – South Loop (1120 South Michigan Avenue) Hot breakfast spot!
  • Harold’s Chicken Shack (612 South Wabash Avenue) Ask for the mild sauce.
  • Lou Malnati Pizza (805 South State Street) Amazing pizza
  • Italian Village Restuarant (71 West Monroe) One of the best Italian restaurants
  • Devil Dawgs (767 South State Street) Best Chicago-style hot dog.  Oh my God, the french fries – skins on, salted to perfection and taste great slathered with ketchup.




where to stay in chicago


Chicago Riverwalk Hotels


  • Radisson Blu Aqua – (221 North Columbus Drive) – Radisson Blu 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 of modern chicness to their Aqua Suite that’s 1732 square feet.


  • Directly across the street from the Radisson Blu Aqua is the Fairmont Chicago (200 North Columbus Drive).  Enjoy the view of Lake Michigan, Millennium Park and the Chicago skyline. Give yourself a treat by visiting the spa.  The Fairmont features hypoallergenic rooms.  Rooms range from 420 square feet of contemporary, subtle decor to their 1200 square feet Grand Suites. (Hello? Who doesn’t love a 1 1/2 bathroom suite?)


  • Chicago Hyatt (151 East Wacker Drive) –  Every time I go inside the Hyatt I’m petrified that I’ll get lost; it just that huge. And there’s a reason why it’s massive – a lot of big conferences are held here.  What I love about the Chicago Hyatt is the rooms are very friendly, and the hospitality is top-notched. It’s located one block from the Magnificent Mile and just steps away from the Riverwalk.  Rooms range from 335 square feet of contemporary lodging to their 2296 square feet luxurious hospitality suite (fireplace included). One of the best hotels to stay in Chicago.

Recommendation: Check out the restaurants and shops at the Illinois Center which is connected to the Hyatt’s lower level via the Chicago Pedway.  This is a great option if you want to take a little stroll and get something to eat but the weather ain’t that great.

  • Swissotel Chicago (323 East Upper Wacker Drive) – A gorgeous hotel located where Lake Michigan meets the Chicago River. The Swissotel is a 4-diamond glass triangular hotel that offers wrap-around views from Navy Pier to Millennium Park.  Rooms range from 319 square feet of elegant comfort to their 1200 square feet 2-level loft suites.


  • The River Hotel (75 East Wacker Drive) – Located on the South Bank of the Chicago River, the River Hotel is a stylish but not overly expensive boutique hotel. The rooms are small, but the location, price, and views of the Chicago River are fantastic.


where to stay in chicago

Neighborhood Snapshot – Wacker Drive/Riverwalk Area

I feel that that Wacker Drive/Riverwalk area deserves its section.  If you check out a Chicago map of downtown you will notice that Wacker Drive follows the Chicago River and creates this curvy crack between the Chicago Loop and the neighborhoods north of Wacker.

If you choose to stay in one of the hotels Chicago downtown on Wacker Drive, you’ll get to see the differences between the city’s multiple personalities.  It is the dividing line between the town that works and the town that plays (and shops).

Most hotels along Wacker Drive/Riverwalk have the most magnificent views of the Chicago River.  It’s going to be hard to choose just a couple of hotels in each category!

What to do Wacker Drive/Riverwalk

where to stay in chicago

For more information on the 10 Best Chicago Tours, Excursions and Activities, click here!

River North Hotels


  • 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 views of Chicago that will take your breath away. Expect spacious rooms with floor to ceiling windows.  Rooms range from 516 square feet (which is huge for a standard room) to their 2700 square feet Infinity and Regent suites.


  • 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 own 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.


Recommendation: If you love amazing seafood, check out Shaw’s Crabhouse (21 East Hubbard St) then head over next door to Andy Jazz Club (11 East Hubbard St) to listen to live music.



  • Best Western River North (125 West Ohio St) – 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 the Hard Rock Cafe. The rooms have been updated since I last stayed there.  They have a sleek, modern flair that the Best Western brand is now known for.
  • Homewood Suites Chicago Downtown (40 East Grand Ave) – Newly renovated in 2016, the Homewood Suites Chicago Downtown is located in the perfect location for shopping and dining.  You will enjoy their complimentary breakfast and complimentary evening social.  Suites range in size from 340 square feet to 531 square feet and come with a full-size refrigerator in the kitchen area.

Neighborhood Snapshot – River North

Photo by Evelina rosic on Unsplash

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.

If you get a chance head over to the Merchandise Mart (owned by one of the Kennedys), up until a decade or so, this building had its very own zip code…yes it’s just that big.  Architectural buffs will appreciate its art deco beauty.  Designers will understand what goes on on the inside of the Merchandise Mart – showrooms and design wholesalers. Foodies will love its food court.  Read more about the history of the Merchandise Mart by clicking here.

What to do River North

  • Chicago Riverwalk
  • Merchandise Mart
  • Willis Tower (Skydeck)
  • House of Blues

For more information on the 10 Best Chicago Tours, Excursions and Activities, click here!


Chicago Hotels Magnificent Mile and Streeterville



  • The Peninsula (108 East Superior St) – Where “Far-Eastern graciousness meets with Midwestern hospitality.” A 5-star luxury hotel featured in Travel and Leisure Magazine as one of the “World’s Best”! The Peninsula is known for its excellent hospitality and deep ties to the community.  Rooms range in size from 531 square feet to the 793 square feet Executive Suite — one of four 5-star hotels in Chicago.


  • Sheraton Grand Chicago (301 East North Water St) – 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/meeting facility.  But that doesn’t mean you won’t be wowed by its hospitality and amazing views of the city. The Sheraton Grand is within walking distance of the Mag Mile and a short Uber ride to Navy Pier.  Rooms range in size from 332 square feet to their 800 square feet Illinois suite.


  • Chicago Marriott Downtown Magnificent Mile (540 North Michigan) – Step right outside the Chicago Marriot and be ready to shop on the Magnificent Mile.  Yes, that’s right. This hotel is located right on the Mag Mile! Newly renovated rooms that range in size from 249 square feet to their much bigger sized suites.

Recommendation: A great way to get around the downtown area is the BigBus Hop On-Hop Off Tour.  It stops at most of the major attractions, and it’s a great way to get to know the city.

where to stay in chicago



  • Fairfield Inn & 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 bedroom decor that is very inviting.  Rooms range in size from 205 square feet to the 330 square feet.


Looking for downtown Chicago hotels near Navy Pier?  I recommend the following places to stay:


Neighborhood Snapshot: Streeterville

It is a toss-up between Streeterville and the area of the Loop between Michigan Avenue and State Street; Roosevelt and Lake Street as to my favorite part of the city to stay and hang out. Pick either area of downtown Chicago to stay, and you won’t go wrong.

where to stay in chicago

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.


Tip:  When exploring Streeterville, I recommend sticking to the side streets which gives you a better feel of what Streeterville is all about. It is hugely residential which I think makes this area interesting. You will miss out on the friendly, neighborly atmosphere of Streeterville if you restrict exploring to the major street that runs through this part of the city; Michigan Avenue.

where to stay in chicago

Every time I come to this part of the city, I’m reminded that back 100 years or so there was no Streeterville – just Lake Michigan.  Yes, Streeterville was built from the Chicago Fire’s debris.  It sits on top of a landfill.


What to do in Streeterville

  • Magnificent Mile
  • Navy Pier
  • Tribune Building
  • Wrigley Building
  • Chicago Lakefront Trail
  • Hancock Building (now known as 875 North Michigan Avenue)/360 Chicago Observatory)


For more information on the 10 Best Chicago Tours, Excursions and Activities, click here!

where to stay in chicago

Tips on booking Chicago hotels downtown deals

The best times to book Chicago hotels downtown deals are late November, early December and the month of February.  March and April are when the price starts to soar for any hotel in downtown Chicago in anticipation of the change in weather.

Book your downtown Chicago hotel stay from Sunday-Wednesday for cheaper rates.  Prices go up on Chicago downtown hotels as the weekend approaches.

Affordable hotels downtown Chicago

The following hotels offer the best hotel downtown Chicago deals and are my go-to when looking for great rates for hotels Chicago downtown; no matter what season.

What’s awesome about these hotels in Chicago downtown is that there are in great locations along with being affordable.  But caution: these accommodations book super fast.

Inn of Chicago

Traveling solo this spring on a budget?  Check out the Inn of Chicago (162 East Ohio) for a good location near the Magnificent Mile and great value for your money.

where to stay in ChicagoHotel room Inn of Chicago, courtesy of

Nearby attractions to Inn of Chicago

  • Mag mile: 5-minute walk
  • Navy Pier: 15-minute walk
  • Chicago Lakefront: 30-minute walk/run – great for walkers/runners
  • Shopping at Water Towers Place (835 North Michigan Ave): 10-minute walk
  • Museum of Contemporary Arts (220 East Chicago Ave): 10-minute walk

Where to eat or drink

  • Ron of Japan (230 East Ontario St) – my favorite absolute best hibachi-style Japanese food
  • The Capital Grille (633 North St. Clair St) – steak and chops
  • Timothy O’Toole Pub (622 North Fairbanks Ct) – my favorite – fantastic chicken wings and beer
  • Yolk in Streeterville (don’t miss this one for breakfast- crazy long wait for a table – it’s just that good)
  • Purple Pig (small plate fare and excellent wine list – not to be missed and just cute)
  • Whole Foods
  • Trader Joes

Best Western River North

Another excellent budget hotel choice is Best Western River North. This hotel has been updated into the new BW modern upscale style and looks nothing like the Best Western River North I stayed in back in the 90s.  The area has changed a lot as well (in an excellent way).

where to stay in Chicago
Best Western River North, courtesy of

Nearby attractions

  • Mag Mile (15-minute walk)
  • Navy Pier (30-minute walk)
  • Tribune Tower (15-minute walk)
  • Wrigley Building (15-minute walk)

Where to eat or drink

  • Hard Rock Cafe (infamous)
  • Meli Cafe (for breakfast)
  • Blue Chicago (find the time if you’re into blues or not)
  • Gino East (excellent deep dish pizza)
  • Lou Malnati Pizzaria (fantastic pizza)
  • Redhead Piano Bar (cute classic cocktail lounge)
  • Portillo’s (great hotdogs, Italian beef (dipped or not), and bacon burgers…oh God I just remembered their milkshakes – Portillo’s crazy busy and crazy good)
  • Chicago Chophouse – one of the greats of the chophouses in Chicago – not to be missed)



Motels in Downtown Chicago

Cheap hotels, downtown Chicago are few and far between, seedy and not worth mentioning except the Ohio House in the River North Area.  This affordable hotel is a motel that used to be seedy but has cleaned up its act…hugely.  The rates at the Ohio House are dirt cheap for the downtown River North area.  And with its location on Ohio Street (15-minute walk from Michigan) you can’t beat it with a stick.

where to stay in chicago
Ohio House Motel, 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.

Chicago hotels north of downtown

Claridge House

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.

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



Hostels Chicago Downtown


If you are looking for cheap but excellent accommodations, a great option would be staying at one of Chicago hostels located downtown.  I recommend HI Chicago Hostel in the Chicago Loop area – great location!

where to stay in Chicago
HI Hostel Downtown Chicago, courtesy of


Click here for more information from Hostel World.


Downtown Chicago Hotels with Pools

The following hotels downtown Chicago from above have pools:



where to stay in chicago

Cost of staying Downtown Chicago – what to expect

Hotel prices in Chicago fluctuate depending on what’s going on in the city and proximity to downtown. Because the downtown area is the hotbed of activity in Chicago, hotel rates are higher downtown than in the surrounding suburbs. Prices go up on Chicago accommodations as the weekend approaches.

Expect downtown Chicago accommodations to fill up quickly during the summer months, which is when the city is in festival mode, and a lot of conventions are in town.

It is still possible to find hotel deals during the summer if you’re willing to do a little research.  You want to make sure to check out what’s going on in town (read my post 17 Chicago Festivals and Events You Don’t Wanna Miss) and plan your visit for the beginning of the week to save money on nice hotels in Chicago downtown.

Book well in advance for summer travel to Chicago.

Warning about booking Chicago lodging

Some hotel chains such as Marriott, Hyatt, and Hilton have more than one hotel located in downtown Chicago.  For example, Residence Inn has 3 different locations in the downtown area: Residence Inn Chicago Downtown Loop Residence Inn Chicago Downtown/Magnificent Mile Residence Inn Chicago Downtown/River North.

Be sure to check Google Maps for the location to be sure you’re booking the correct Chicago lodging in the location you want to stay. And just because the name of the hotel says “Magnificient Mile or “Downtown” doesn’t mean its actually on or very near that location.

Check out the reviews on TripAdvisor before booking rooms in Chicago.  Do the research!

where to stay in chicago


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For more information on Chicago, check out the following articles:



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