Chicago Travel Guide

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I wanted to write this Chicago travel guide to share my love of Chicago with you. It’s rare that you find a major American city so affordable as Chicago, as long as you make wise choices about how to spend your money. I’ve visited as a solo traveler and also as part of a couple, so my perspective won’t take into account young families where kids tire easily and need their own custom fun. When I did my research, I found all types of advice, good and not so good. If you buy a notable guidebook, like the Lonely Planet Chicago guidebook, and then do your own online research, you should be able to plan a great trip.

Be Neighborhood Friendly

Like any city, Chicago is made up of many neighborhoods, some close and some quite far from the central Loop. If you want to understand Chicago, you should intentionally visit some of these neighborhoods, since that’s where people live, eat, and play. Many people travel to the Loop to work, but few actually live there. Go through your guidebook and create a list of neighborhoods with sites in each that you want to visit, and work these into your plan. For me, it’s sort of like travel bingo!

Don’t be afraid to plan too much, then find that you have to pare back as you go. Allow a bit of randomness to work its way into your trip, including on the spot recommendations from the locals you meet who might very well a great idea that you should try. Make your own memories and don’t have the same trip as every other tourist.

How to Travel

The Chicago Transit Authority (CTA) offers 1-day, 3-day, and 7-day unlimited passes through a Ventra card and accompanying mobile apps. The Ventra card unlimited passes include all CTA L trains and buses, but not the Metra trains. However, the Ventra card and app can be used to purchase Metra train tickets as needed. Before you go, figure out before you go to what extent you want to use the CTA system so you’re ready to act when you arrive at the kiosks at O’Hare or Midway airports.

Do you need to rent a car? It depends on what you want to do, and how many people are with you. Public transit options become financially less attractive as your group gets larger. However, whether you are one or six, parking your car in the Loop, including overnight at your hotel, is going to be very expensive.

Therefore, think about where you want to visit. If you interests cover neighborhoods further out and perhaps some suburbs, consider renting a car for just part of the time, even just a final day. Even transit fans like me will admit that taking the green line out to Oak Grove, walking to the beginning of where the Frank Lloyd Wright houses begin, doing the walking tour, then reversing your path back to the city, makes for a long day. Transit does a better job the closer in you are to the Loop.

Renting a car at the end of your trip has several advantages. You’ll avoid all of the extra taxes and surcharges from renting at the airport. Plus, you won’t have to pay for parking your car in the city on days you don’t use it. You get the added benefit of convenient transportation to the airport at the end of your trip. And the clincher might be this: You are likely to find a less expensive hotel in the suburbs.

How to Save a Bundle

Don’t bundle! That is, don’t succumb to buying the heavily advertised pass programs that profess to save you time and money, but cost you dearly in terms of both! The full retail cost is around $100 for adults, and just a fraction less for kids.

If you like the idea of only doing the most expensive activities, and chasing around the city to make sure you get your value, this type of deal might be for you. I’d rather take my chances paying for what I do à la carte since my interests are far more diverse than the very limited options offered in these programs. Plus, I may just not have the energy to do three big things in one day and instead want to enjoy a leisurely lunch or dinner at a neighborhood restaurant instead. Even if you just want to have pizza or hot dogs, eat them at a place famous for them, not at the snack bar at a tourist trap!

I challenge you to create your own pass program. Choose one or two sites expensive sites, then combine that with some of the inexpensive and free options listed later in this guide. You will be the one saving the money!

Your biggest expense besides activities and meals will be your hotel. If you are paying cash for a room, versus staying on points or miles, try to visit when business travelers aren’t there! Chicago has some of the largest hotels in the U.S., and room rates will drop dynamically in order to fill those rooms. Generally speaking, you’ll get better rates on weekends than during the week, unless there are major conventions or peak tourist weekends. Even something as trivial as a one-day holiday, like Memorial Day or Fourth of July, will discourage business travelers from visiting during that week, benefiting you if you can stay on those weekdays.
Thanksgiving and Christmas are some of the absolute cheapest times to visit. Dig around for a fabulous rate, and take a look at the Choose Chicago Website, where I once found a $150 rebate on a 3-night stay during Thanksgiving at my choice of hotels from a very long list of participants.


Walk some of the many bridges over the Chicago River. Walk Wacker Drive south of the Chicago River. Many of the cities great skyscrapers can be seen from this one arcing road.

The Lincoln Park Zoo is free and is possibly the nicest zoo in the country without an admission charge. It rivals many in smaller cities where you have to pay at the gate. This is just another reason to question whether to purchase a visitor’s pass.

Yes, it’s the ultimate stretch of tourist pavement, but there’s no need to avoid the Magnificant Mile, the nickname for North Michigan Avenue. There are some striking architectural highlights like the Wrigley Building and the Water Tower. Just don’t spend too much time shopping in what are mostly national chains found elsewhere. If you walk North Michigan in one direction, walk the other way on Wabash Avenue. You not only avoid the crowds, but you get to see many historic and neighborhood buildings.

While you’re on the Magnificent Mile, make sure to check out one of the several “escalator” malls, such as Water Tower Place or the Shops at North Bridge. You’ll find some local stores in these, plus services like bathrooms that are their own reward for entry.


Consider doing the Chicago Architecture Foundation Docent-Led Chicago River Cruise. It’s worth every penny! There are several groups offering low-cost walking tours, but there’s also Chicago Greeter, offered through the Chicago Visitor Center, which offers walking tours for free. However, it’s hit or miss. I’ve not been successful in arranging a volunteer guide for where I wanted to visit, when I wanted to visit.

Intentionally choose one place to visit that is inexpensive and unique. If you like art, try the Museum of Contemporary Art. If you like history, maybe it’s the Chicago History Museum. Or, it could be an Improv show at Second City. This is one sure way to be able to tell a vacation story that isn’t the same as everyone else who has visited.


Although I’ve seen the Bulls and Blackhawks at the United Center, even the cheap seats at face value are really expensive. Certainly Bears tickets will be expensive and hard to get. If it’s a once-in-a-lifetime thing, maybe go for it?

Otherwise, if you’re visiting in the spring and summer months, you have soccer and baseball. The Chicago Fire is the Major League Soccer franchise. Tickets are typically more reasonably priced than for baseball, though the stadium is far from the Loop. Given that you have both the Cubs and White Sox, you have a good chance that one of the baseball teams will be in town at any one time. Don’t be discouraged about going to a Sox game at night. Certainly, you can’t walk around the neighborhood like you can at Wrigley Field, but if you take the L directly to the ballpark at 35th Street, then take it straight back, you should be fine.


Even though my best eats have been in neighborhood restaurants, I have some favorites when starting or ending my day in the Loop. There are tons of options – use apps like Yelp or Zomato to find what you want. In particular, I love breakfast spots like the small chain Yolk. However, be advised that during weekends and holiday periods, these places are packed with often insufferable waits. Go early or go near closing. Their appeal lessens if you have to burn an hour of waiting just to get seated. That same thing can be said for many popular restaurants during peak hours, such as Giordano’s.

If you’re flustered, short on time, and just need healthy food at affordable prices, Whole Foods, like the one in Streeterville, offers a buffet all day long. There are many coffee and sandwich shops that offer sandwiches, salads, yogurt, and the like, with no wait.

Coffee Culture

I’m a huge fan of third-wave coffee, and Chicago has many local options. Intelligentsia and Dollup are just two of them. Why not take a break to refuel, check your email with free wi-fi, and get a snack at reasonable prices? Pour-over coffees at both places did not exceed $4 during my visit in February 2018.

Not Just for Tourists

Garrett Popcorn – You might think that Garrett is just a tourist thing since they have two stores at O’Hare, but no, that’s not the case. It’s okay to stop to pick up a bag or two for eating during and after your trip. I love the small souvenir quart tins that are sold at most stores for just a bit more than $14, tax included. However, you won’t find these at the prime tourist shops on Michigan Avenue, which purposely don’t carry these in order to upsell you to the more expensive, bulky gallon buckets. If you’re not interested in the gift tins, just go to any store!

Vosges Chocolate – The name might be French, but the chocolate is from Chicago. They make bar and boxed chocolate. And like Garrett, they also have two locations in O’Hare Airport.

Finding Your Way

Avoid walking around the city with your phone constantly in your hand. Besides the warning given under the Safety heading, you’re bound to irritate the locals with your inattentiveness. You’re also going to miss some incredible architecture.

Navigating in Chicago is really easy with your phone in your pocket! The city is oriented perfectly on compass points. Plus, its streets are organized in the typical midwest grid system, with Madison and State being at (0,0). If you know where you are, and you know where you need to go, use the building numbers and street signs to help guide your way.

You’re probably not surprised that I carry an old-fashioned compass like the Brunton TruArc3 Baseplate Scouting Compass and a small tourist map. However, I’ve also used the compass app on my phone when I’ve forgotten the physical one. I check them from time to time but then put them promptly away. You can get a small pocket map from your hotel, or better yet, buy a Streetwise Chicago Map before your trip. Anywhere I go, even to cities I know well, I carry this brand of map.


Don’t rely on your guidebook to warn you about safety. For instance, the Lonely Planet Chicago guidebook, which I otherwise heartily recommend, doesn’t warn you where to use extra caution. They do give the great advice not to flash your cell phone everywhere you go since that leaves you vulnerable to its theft. Plus, it makes you more vulnerable in general.

Inside the Loop, which has many but not all of the popular tourist destinations, you are generally fine, though exercise caution late at night, like in any big city. If you venture outside the Loop, use a combination of research and common sense to gauge your risk. If in doubt, ask at your hotel, or if you’re already out and about, speak to transit personnel or shopkeepers. There are no-go neighborhoods on the South Side and elsewhere, which are unsafe even in the daytime. Don’t be discouraged from crossing them to get to your safe destination, just be sure to use some method of transit all the way (L, bus, Metra train, or car).

Chicago drivers are aggressive. This is something you’ll learn pretty quickly, and hopefully not the hard way. Don’t be on auto-pilot when crossing streets, even when you have the right of way. Cars will often pull forward into the intersection to make a right on red, or just for pole position for the next green light, whether or not you happen to be in their way. If you know the acronym YCDS (Yellow Cars Don’t Stop) from visiting New York City, double this awareness in Chicago.


It gets cold and windy in the winter and hot and humid in the summer. Plus, it rains and snows a lot. This isn’t Aruba. Fortunately, being prepared is pretty easy, thanks to 10-day weather forecasts. It should be pretty easy to switch outdoor activities for indoor ones, if necessary.


Feel free to share what you love about Chicago, or what you look forward to doing on your next trip!

Last Updated 2018-03-08 | Originally Posted 2018-03-05