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This travel guide helps you prepare & plan your trip to Chicago. It covers where to stay, how to get around, what to pack & what to do. I will also share some tips, tools & products to help make your stay a memorable one and save you some money.
getting here
Personally, I use Expedia to search for flights when I have the itch to get out of town to explore a new part of this big, beautiful world. It’s super easy to search for the best price for flights. They also have alert options to keep an eye on your flights. Booking.com
where to stay
Now that you have a handle on flights, next on the list is where to stay. I would suggest either a condo rental or one of the many hotels available. Go with vrbo a condo rental if you want to experience living like a local since it will most likely be in a neighborhood. Bucktown, Wicker Park, Logan Square & West Town are all great Chicago neighborhoods to stay in where everything (cafes, restaurants & bars) is easily accessible, walkable, or a quick ‘L’ or rideshare to downtown. Hotels are a good choice because they have many locations throughout the city (& some neighborhoods) and amenities like gyms, pools, spas, or rooftops with spectacular views.
You could always look into a hostel if you prefer the budget route. Click here for some options.
Based on my client ratings, here are some great Chicago hotels to stay in: the Sofitel, the Four Seasons, and the Park Hyatt (all close to The Historic Water Tower & Magnificent Mile), the Thompson (near Rush St & the Gold Coast neighborhood), the Langham (near the Chicago River & Riverwalk) and the Chicago Athletic Association Hotel (Cindy’s rooftop & across the street from Millennium Park). Click here for more budget friendly options.
how to get around
Once you have figured out your lodging, transportation is next on the list. How does one get around a big metropolis like Chicago? Easy, you have multiple options. But make sure you bring good walking shoes (see my recommendation below) because Chicago is a walking town. Get around by walking, biking, taking public transportation, grabbing a cab (yes, we still use those occasionally), or rideshare. You should also try the water taxi, depending on the season.
No rental car is needed if you are staying in the city. Believe me, if you can avoid driving, you should. Even if you are here for a work conference in the suburbs, check with your hotel to see if you are near an ‘L’ line or the Metra train (the commuter train that gets suburbanites downtown). Hotels in the suburbs may have a shuttle.
public transportation
Here are some tips for taking public transportation (the ‘L’ or the bus). ‘L’ stands for elevated, as in the elevated train that goes above ground & traffic. There are eight lines total (Red, Blue, Brown, Green, Yellow, Purple, Orange & Pink). We call them all the ‘L’ even though some lines are elevated & some lines go underground (the subway). Interesting fact: The ‘L’ is over one hundred years old! The first line that ran to Jackson Park was a people mover, getting them to the World’s Columbian Exposition of 1893.
You can purchase a Ventra card at any CTA (Chicago Transit Authority) station, and it can be used on both the train for $2.50 & the bus for $2.25. You can get a good transfer for two additional rides within 2 hrs for a quarter. Depending on the duration of your trip, you can purchase a 1, 3, or 7-day pass, and they cost $10, $20 & $28.
Download the Ventra app. You can check your Ventra Card’s balance, add value or passes, get arrival/departure times and account alerts. You can also use the fare value from your Ventra transit accounts to buy mobile tickets for riding Metra trains as well. Also, I would suggest using the cta trip planner to get around. Plug in your starting destination and where you are going; it will give you options for different routes.
I don’t have a car for many reasons, and one of them is that Chicago is easy to get around without a car. Plus, you see the city differently on a bus, train, or bike.
You can take the ‘L’ in from either airport. Take the Orange Line from Midway or the Blue Line from O’Hare. That is if you don’t have a lot of luggage since it’s much easier to navigate if you travel light and have only one bag. Look for escalators or elevators at cta stations. If you are schlepping a lot, then a taxi or rideshare is the better choice.
theatre
Chicago is a great theatre town with traditional holiday classics like The Nutcracker & A Christmas Carol, and many more. If you are a theatre buff, click here for many options. Also, check out Hot Tix for half-price tickets. My favorites are Theatre on the Lake, the Steppenwolf, and the Looking Glass Theatre (housed in the Historic Pumping station across the street from the Historic Water Tower) for their creative productions and interesting history.
Looking for dance & musical theatre? Check out what’s at the Joffrey Ballet, the Lyric Opera & the Harris Theatre! Interesting fact: Theatre on the Lake was a sanitarium for sick children back in the late 1800s/early 1900s. It was open air, and the kids slept in hammocks. The fresh lake air was thought to cure babies suffering from tuberculosis and other diseases.
How about a magic show? I’ve heard really good things about the Chicago Magic Lounge in Andersonville. Check out Goldstar for discounts on tickets for many different experiences.
where to eat
Chicago is a great city for foodies. Lately, I’ve been using Google Maps to decide where to eat. Traditionally, restaurants come and go, and sadly, many places are closed due to the current state of things. Bring it up on your phone, and it will show you what is currently open near wherever you are. I predict increased foot traffic from worker bees & tourists in the Loop, and new restaurants will rebound. Your best bet, for now, is to check Google Maps since it should be pretty current & accurate.
Here are my favorite lunch spots when I’m in the Loop. Cafecito, BienMeSabe, and Revival Food Hall. Revival Food Hall has the best neighborhood restaurants altogether in one spot. So many delicious options to choose from! Before everything shut down last year, food halls were a huge, new trend. I hope that they will indeed come back. Click here for the latest info on the food hall options. Here’s my BienMeSabe blog post.
Want to try a Chicago-style hot dog, pizza (thin & deep-dish), or a beef sandwich? Click here to find out where to get some iconic Chicago food staples. And here’s my advice regarding the pizza: while deep-dish can be AMAZING, take it slow. Get a pizza and a big salad to share and a nice glass of wine or local beer. Trust me here: you don’t have time for a food coma to slow you down. When I’m craving deep-dish (and I’m a thin-crust girl), my go-to is Pizzeria Uno & Due and Lou Malnati’s fresh out of the oven.
We have a lot more incredible food besides the Chicago classics. If you feel like exploring and checking out some of our 77 Chicago neighborhoods, here are some updated new & essential restaurants. For the record, when I crave Indian food, I go to Devon Avenue in Rogers Park. Mexican? Pilsen. Pho? Argyle Street. Dumplings? Chinatown. While there are some excellent restaurants (food halls!) in the Loop, you should venture out to the neighborhoods for various delicious options. Attention foodies, this just in: Michelin’s Chicago Bib Gourmands. What is a Michelin Bib Gourmand, you ask? It is quality food for good value. Didn’t I mention that we have way more than pizza, hot dogs & beef sandwiches?
best weather
The best month for Chicago weather, IMHO, is September. You still get late summer warmth, but activities are slowly winding down. The second best season is summer (June – August), where there are almost too many things to do, but that’s a good problem to have, and the weather is more moderate. But remember, the weather here is fickle, and you need layers to be prepared for your perfect 3-days in Chicago. Even in the Summer, temps can plummet, and you will feel it if you are downtown near the lake, Lake Michigan, that is. If the wind switches direction and comes in from the north, it could drop 10-15 degrees in a matter of minutes. That’s why we have so many wardrobes here! I know it sounds like an excuse to shop more, but being prepared makes a world of difference.
what to pack/wear
Chicago is very walkable, so good walking shoes are a must. Admittedly, I am a shoe freak and always on the hunt for cute & comfortable walking shoes. Being a tour guide, I’m on my feet all the time, all year round, and getting a blister or having achy feet just won’t cut it. I’ve done a lot of research for the last 10+ years, and here are my walking shoe recommendations.
For all-day tours, I recommend good supportive shoes (lol…so does my podiatrist) like Asics, Dansko, or Vionic brands. I’ve worn Asics since my running days and was hooked the moment I tried them on. They come in a variety of great colors and have a range of prices. Dansko & Vionic have many cute, supportive sandal styles when you just need a break from sneakers.
I also like Allbirds. Super cute & comfortable, and that’s not all. They are ethically & sustainably produced using wool & their shoelaces are made out of recycled plastic bottles! I’m horrified and can’t even imagine the global waste from this past year of being locked down, so every little bit helps. And they are machine washable. My go-to’s are the Tree Skippers style (Jet Black with White Sole). I have friends who swear by these for long distances, and while they are really comfortable, I wear them for short tours.
Other must-have staples are a hat, sunglasses, sunscreen, and a lightweight, packable jacket with a hood. I like hats with a small brim to keep the sun off my face. And since I’m pretty much out every day from spring through fall, this is important to me. During the thick of the summer, I usually go for a straw hat with a bigger brim for more sun protection like this one.
I am a Ray-Ban girl and always have been. I switch between two pairs. Of course, even with sunglasses and hats, I still wear sunscreen. I discovered Supergoop! Sunscreen (for face & body) last summer. It’s a hydrating, nourishing, broad-spectrum product made with natural ingredients & reef-safe. And don’t forget good deodorant! Speaking from experience, it was hard finding one that would last through an all-day tour. I’ve tried so many natural deodorants without any luck until I found Lume. It smells great, has clean ingredients & actually works! I also love their soap & deodorant wipes.
This may sound a little crazy, but I wear cashmere all year round. I have a cashmere wrap I use for traveling and a cashmere cardigan that I use as a light jacket. I just discovered Quince, an eco-friendly, reasonably priced cashmere line. It is worth a peek because they also have a great selection of high-quality natural fabrics besides cashmere and great price points.
A lightweight, packable jacket with a hood is handy for rainy days, eliminating the need for an umbrella.
books
I rarely read ‘normal’ books anymore. They pretty much consist of books on Chicago history, not that I actually mind though. Here are a few recommendations.
The Devil in the White City by Erik Larson. Required reading for Chicago history nerds and docents in training covers the building of the White City (World’s Columbian Exposition in 1893) & murders happening simultaneously. Fascinating & gruesome!
Clara and Mr. Tiffany: A Novel by Susan Vreeland. Historical fiction tells a tale about a talented young woman and her experience working behind the scenes for Louis Comfort Tiffany.
The House on Mango Street by Sandra Cisneros. A poignant story of a young girl’s experience growing up in Pilsen, a west-side Chicago neighborhood.
The Jungle by Upton Sinclair. Not an easy read and you may very well become a vegetarian. A gritty glimpse back in time to the Chicago Stock Yards. Prompted the creation of the FDA.
discounts/deals
Get a cityPASS to save you money on tickets for mutilple Chicago attractions including museums, river cruises & more!
Another great way to see the city when you need a break from walking is the BIGBUS tour. They offer a Shoreline Sightseeing 75-minute Architecture Cruise and Esentia; Bus tour. They also added a Sunset Live route that is just magical!
Check back often for more recommendations!