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What You Should Know about Chicago Downtown
In the last 5-10 years, Chicago has experienced a reverse migration of its population with people leaving the suburbs to live downtown. We baby boomers figured out what the young folks have always known – that downtown Chicago is where it’s at.
Downtown Chicago is highly residential. The residents of the downtown area eat, live, work, shop, and play in the downtown area. The city has done a lot to make the downtown area attractive, accommodating, and accessible to residents and visitors alike.
Most residents of downtown Chicago either walk, uber, or take public transportation to get around. The Lakefront is a beautiful backdrop to the downtown area, and you will see plenty of folks, running, biking or strolling along Lake Michigan.
Downtown Chicago Neighborhoods
The following neighborhoods make up the downtown area:
- South Loop
- West Loop
- (Lake Shore East – some Chicagoans consider this neighborhood part of Streeterville)
- River North
- Gold Coast
Getting around Chicago safely
Traffic is crazy. And unless you have a robust constitution or a death wish, I recommend not renting a car while staying downtown. Besides, the price of parking is outrageous, and most hotels don’t have free parking.
The best way to experience downtown Chicago is by walking. Uber, taxi or public transportation are also great options.
The exception to this rule is if your travel itinerary include traveling outside of the downtown area and even then I would only rent a vehicle on the days your travel plans take you elsewhere.
As a visitor, staying in the middle of downtown Chicago will give you a taste of what it’s like to live in the city. Everything is convenient and right at your fingertips.
And as far as safety, a visitor should treat this city like any other metropolitan oasis – with some common sense. That being said downtown Chicago is patrolled by the men and women of the Chicago Police, Chicago Transit Police, University Police/security force (in some neighborhoods) and a host of other law enforcement entities.
In this article, I’ll be discussing where to stay in Chicago downtown neighborhood of the Loop. And I also discuss:
- the best place to eat in Chicago downtown
- top 10 things to do in Chicago downtown
- 4 things you could really skip doing
- best places to stay in the Loop
Where to stay in Chicago Downtown Loop
Each downtown Chicago neighboorhood has its unique character and charm. You will find the Loop neighborhood just as charming and unique as its neighborhood counterparts.
With amazing choices for accommodations, whether it be either hotels or Airbnb, you will love every bit of this Chicago downtown neighborhood.
In this section, I discuss the best places to stay in Chicago Downtown Loop area. Both my choices are great; one is for the traveler who wants to be in the middle of all the action and one is best for the business traveler who wants a little peace and quiet. best hotel options should you decide to stay in the downtown Loop area.
Best place to stay in Chicago Downtown for the best Chicago Loop Experience
The Palmer House (17 East Monroe) says “Chicago” with its Old-School charm with quiet, understated elegance. This hotel is breath-taking. If you’re a history buff or architectural geek, you will want to wander through every nook and cranny of this hotel.
There’s a ballroom, for God-sake! Baby, they don’t make ’em like this anymore. If you have the chance, definitely place this on your hotel bucket list.
The Palmer House location makes it perfect for exploring the Loop area of downtown. You will be close to EVERYTHING –
- a block away from Michigan Avenue
- shopping on State Street
- Millennium Park
- Theater District
- public transportation (Red Line Line Monroe Stop)
It screams EXCITEMENT! You will be smack dabbed in the middle of all the action and walking distance to a lot of attractions and museums.
To take a look at hotel rates and reviews for the Palmer House, click here.
Best place to stay in Chicago Downtown if you want to be away from the action
But what if you want to stay in the Loop but looking for something a little less glitzy and away from the busyness and noise (at least at night)? Then, you will want to go with La Quinta Inn and Suites Chicago Downtown (1 South Franklin).
- a 5-minute walk away from Willis Tower
- a 15-minute walk from the West Loop
- a 20-minute walk from Randolph Street Restaurant Row
- close to major expressways, if heaven forbid, you happen to be driving
It screams quiet, sedate and in your room tucked in before dark because I have to be at a business conference the next morning.
Should you decide to venture out after dark, you will find this corner of the loop near empty. Most businesses close down after the happy hour is over (around 6 PM or so).
Finding somewhere to eat for a late dinner or snack will be a bit difficult in this corner of the Loop. Uber or cab it east toward State Street or Michigan Avenue to get a late bite to eat. Or take transportation to the downtown West Loop neighborhood and check out Randolph Street Restaurant Row.
To take a look at hotel rates and reviews for the La Quinta Chicago Downtown, click here.
Airbnb in the Loop
Airbnb Tip: Filtering your search to Super Host will give you great choices but will most likely cost more. If you’re not too picky, you can find a bunch of bargains with Airbnb in the Loop.
The Loop: Center of the city’s business
The Loop’s rough boundaries are from Lake Michigan to the North, Chicago River to the West and North (it curves around the Loop from North to West) and Roosevelt Road to the South.
Think of the Loop area of downtown as a square with four quadrants and Madison (E/W) and State (N/S) is the dividing line.
Map of Loop area of downtown Chicago
The city’s business is conducted in the Loop. Just looking at that statement, you might be thinking that sounds like an area of downtown I want to avoid.
While one-fourth (think about the quadrant square example I gave earlier) of the Loop becomes silent after work hours the other three-fourths of Loop is still booming with activity once the sun goes down.
There is plenty of good times to be had in the part of the Loop that is vibrant and active after rush hour.
Things to do in Downtown Chicago Loop
Warning: you’re going to have a good time no matter which part of the Loop you decide to stay in. So don’t worry.
During the day hours, the Loop is vibrant with tons of commuters from all over the city and suburbs flowing into the downtown area like a river.
The commuter pedestrian AM/PM rush can be a little overwhelming for the visitor who’s caught in the flow.
Eat Breakfast then Willis Tower
Have breakfast at Goddess and the Baker (33 South Wabash) before the breakfast crowd makes it impossible to find a seat.
Things start to settle down a bit between 9 AM and 11:00. This is an excellent time to check out the Willis Tower (233 South Wacker) before the lines become unbearably long.
Have lunch then Chicago Riverwalk
If you’ve descended from the Willis Tower by 11:00 AM or noon, head over to Luke’s Italian Beef (215 West Jackson) for an Italian Beef sandwich (you will be asked if you want it dipped) and some fries. For healthier options, head to Pret-A-Manger (211 West Adams)
After lunch, head over to the Chicago Riverwalk for a stroll along the Chicago River. Follow the River north then east as it curves around the outside edge of the Loop.
End your walk at the northeast corner of Michigan Avenue and Wacker Drive where you will catch the Chicago Architecture Foundation River Cruise on the First Lady. For departure times and buy tickets, click here.
Dinner and some Blues
After business hours, the majority of the Loop is ready for a reasonable time after a hard day of working. Mix with the tons of folks going out to dinner, going shopping or to the theater.
Best places to eat in Chicago Downtown Loop:
- Berghoff Restaurant (17 West Adams)
- Italian Village Restaurant (71 West Monroe)
- Flat Top Grill (30 South Wabash)
After dinner head over to Buddy Guy’s Legend (700 South Wabash) for some blues – Chicago-style.
How to experience the Loop downtown Chicago
There are plenty of reasons to visit Chicago. And because it’s impossible to fit everything in – I recommend focusing on a theme or interest behind your visit to Chicago.
Here are my picks for what to do in downtown Chicago if you’re interested in the following:
- The Theatre Experience
- Chicago’s History through Architecture
- Museum Lovers
The Theatre Experience
The theater scene in Chicago is HOT! Several great plays (and named actors) are showcased here. There are tons of theater located in the Chicagoland area. Here are some theaters I recommend checking out while visiting the Loop in Chicago. Click on each link to be taken directly to their website.
Chicago’s History through its Architecture
Chicago is famous for its architecture. If you’re an architectural buff, like me, you must take a few architectural tours of the downtown area. Here are some of my favorites:
1. Chicago Architecture Foundation River Cruise – the original one from back in the day and is still my absolute favorite architectural river cruise (there’s a number of them). If you don’t do any other tour during your stay, be sure you do the Chicago Architecture Foundation River Cruise. Click here to research ticket prices.
2. Chicago Walking Tour: Art Deco Skyscrapers – put on your walking shoes and weave in and out of some of the best examples of 1920s art deco in Chicago. Tour guides are certified Chicago Architectural Foundation Guides; they know their stuff! Click here to research ticket prices.
3. If modern architecture is more your thing, then check out Chicago Walking Tour: Modern Architecture that focuses on the Loop’s modern and post-modern additions to the skyline. Click here to research ticket prices.
Oh my God, there are so many museums to see in Chicago. And most of them you could spend a whole day exploring. I recommend not rushing; take your time when visiting my favorites. I can only get through one a day before I start seeing double.
1. The Museum Campus (1200 S Lake Shore Drive) – There are three museums located at this campus.
- Field Museum of Natural History – dinosaurs, mummies, and stuffed polar bears…oh my!
- Shedd Aquarium – Check out the marine life (and check out Jazzin’ at the Shedd during the summer months – click here for more info).
- Planetarium – The age of Aquarius, the moon and the stars are aligned.
2. The Art Institute of Chicago (111 South Michigan Avenue) – One of my favorite museums. It is the museum with the two lions out front. The special exhibits are always changing, so it never gets boring, but the main exhibits don’t get boring either. Be prepared to spend all day at this one. For the true art lover. To research the price of admission, click here.
Best Places to Visit in Chicago Downtown Loop
- Millennium Park
- Chicago Theater
- Hubbard Street Dance Chicago
- Chicago Symphony Orchestra
- State Street Shopping
Four things you could skip if you’re not the touristy type traveler
You know who I’m talking about. The traveler who wants the real, authentic travel experience and don’t want to stand in line and spend a shit load of money on trinkets and refrigerator magnets.
And never shops for souvenirs for friends or family or stupid t-shirts – don’t even ask! Here are my picks for tourist attractions that you might want to skip
1. Navy Pier – if you eat or shop here be prepared to spend a lot of money. An extra amusement tax is added on top of every, every purchase. Don’t eat at the McDonalds; don’t even buy a soda because it will cost you double. If you want, check out the Ferris wheel if you’re not afraid of heights. (I am, by the way).
Instead, check out the events (some of them are free) that are held at Navy Pier year-round. Click here for more information on events and venues.
2. Willis Tower – I know, right?! Willis Tower’s Skydeck is one of those once-in-a-lifetime bucket-list attractions. Do it. Suffer through the long, endless lines and the exciting movie that you have to sit through. Enjoy the view once you finally get to the top. Then let it go – trust me you’re not going to wanna go through it again in this lifetime.
It won’t skip you pass the line to get to the Skydeck, just the line to purchase tickets. There is no fast pass to the top.
3. Avoid the Magnificent Mile if you’re not shopping. Impassable just about most of the day due to tons of people walking…very slow.
4. Deep Dish Pizza – Chicagoans don’t eat deep dish pizza. It’s costly, and you can only eat one slice. And it’s impossible to warm up later because it’s so huge. Maybe every blue moon we might eat this, but we never take the leftovers home for later. I recommend trying it just once to say you had it. Go to either Gino’s East, Lou Malnati or Giordiono for the best. After that always order thin crust pizza.
Top 10 things to do in Chicago Loop
Here’s my list of top things to do in Chicago while staying in the downtown Loop area. Some of these things are not just in the Loop area, but I feel you shouldn’t skip the experience.
1. Architectural River Cruise – if you don’t do the one mentioned in this article, do ONE of them. You will not be disappointed, and it’s a unique way to see Chicago.
2. Millennium Park – ice skate during the winter or splash in the fountains during the summer. Have a drink at the Park Grill. Take a pic of the Bean (Cloud Gate). Check out Movie in the Park (Tuesdays, June – August).
3. Even if you hate art, be sure to get a selfie in front of the Lions of the Art Institute of Chicago
4. Harold’s Chicken at 612 South Wabash – a local chain but this one is my favorite downtown location. Don’t forget the mild sauce. It’s a Chicago thing.
5. Pizza at Lou Malnati – it will change your life, and you will never want pizza from anyplace else.
6. Drinks at the Signature Lounge on the 95th floor of the Handcock Building (now called the 875 North Michigan Avenue Building). Go during sunset.
7. An evening stroll (or jog) along the Lake Front
8. A selfie in front of Buckingham Fountain. Go back at night and watch the light show.
9. Lunch and wine at the Walnut Room in the old Marshall Fields Building – now Macy’s at 111 North State. Check out the huge Christmas Tree at during the holiday season
10. Baseball Game at Wrigley Field (if in season) – one of the last great old ballparks. Even if you hate baseball, you will love the neighborly vibe of the neighborhood of Lakeview. After the game slip into one of the many taverns in the Wrigleyville/Lakeview area for a beer and great local baseball commentary.
Getting to Chicago
2 airports service the Chicagoland area; O’hare Airport (ORD) and Midway Airport (MDW). You are going to have plenty of ground transportation options once you land. However, the fastest and cheapest way to get downtown is by public transportation. Both airports are easily accessible by public transit; the Chicago ‘L’ trains.
Traffic from the airports is horrible unless you fly in very early or late (after 7 PM). Unless you love sitting in mind-numbing traffic, I recommend taking the ‘L.’ During rush hour (6 AM- 10 AM and 2 PM – 6:30-7PM), it can take up to 2 hours to reach downtown from either airport (even though MDW is a lot closer to downtown).
Three expressways run through the Chicagoland area: Interstate 90/94, Interstate 55, Interstate 290.
More articles on Chicago:
- Where to stay in Chicago: An Insider’s Guide to Chicago’s Hotels
- 17 Chicago Festivals and Events You Don’t Wanna Miss
- Top Five Things To Do This Weekend in Chicago