I cannot believe it took me so long to finally travel to Chicago! It is quick and easy to get there from nearly all U.S. cities, as O’Hare Airport is the most connected airport in the country due to its central location. I was only there for three days, which made for a perfect weekend getaway. Chicago has a little bit of everything – a food scene, historic architecture, day-to-night entertainment, and a beautiful lake. Keep reading for my first timer’s guide to a weekend in the Windy City!
In this travel guide, I will share my tips for where to stay, what to eat and drink, and things to see and do in the third largest U.S. city.
Table of Contents
STAY
Chicago has plenty of major hotel chains to choose from when looking for accommodations. Many of the bigger hotels have rooftops, too (yay)! When looking for the best area, I recommend The Loop / Downtown, River North, or the Magnificent Mile. We chose to stay at Hyatt Centric The Loop, as we were primarily in Chicago for a wedding downtown and it was close to the venue. Aside from the convenient location downtown, our room was amazing – we got upgraded to a spacious corner suite with panoramic views of the city. Don’t miss the rooftop bar!
Tip: Create an account with all the major hotel chains so that you can reap the benefits that get better and better the more you stay (free Wi-Fi, room upgrades, higher floor rooms, etc.).
Alternative: Chicago Athletic Association
EAT
Living in New York City, I am spoiled with the very best food, but let me tell you…Chicago does not disappoint!
BRUNCH
True Food Kitchen, Maison Marcel, Chikatana, Beatrix
LUNCH & DINNER
Deep Dish Pizza: Lou Malnati’s, Pequod’s Pizza, Giordano’s, Gino’s East, Pizzeria Uno
Tip: Most of the pizza spots in Chicago do not take reservations, but you can try calling ahead to join the waitlist. Lou Malnati’s even has an virtual waitlist that you can join on their website.
Burger: Au Cheval (this is a Chicago original with a second location in NYC – it is my favorite burger ever)
Pasta: Ciccio Mio, Osteria Langhe
Everything Else: Time Out Market Chicago
DRINK
COFFEE
Foxtrot Market, Fairgrounds Coffee, Hero Coffee, Metric Coffee
COCKTAILS
Beatnik on the River, Cindy’s Rooftop
SEE AND DO
Chicago and New York City have a lot in common when it comes to attractions and entertainment. Both destinations offer skyscrapers, shopping, sporting events, parks, theaters, and museums. Of course, New York City is my preferred city (and my home), but you will not get bored in Chicago!
SEE THE ARCHITECTURE
I highly recommend that you prioritize booking an architecture river cruise. There are multiple companies to choose from, but we really enjoyed the Summer of George tour. There was a lot to learn about the styles of architecture and the controversies behind the history of each building, but our tour guide didn’t overwhelm us with information. The views were amazing!
EXPLORE THE PARK
Grant Park is home to Millennium Park (hint: the famous Bean), Buckingham Fountain, the BP Pedestrian Bridge, The Art Institute of Chicago, and pretty little gardens. Grab a coffee and take a stroll!
If you are ready to keep walking, make your way to the Magnificent Mile – an iconic shopping district.
If you are looking for more than just city vibes, head to Wrigley Field for a Cubs game or to one of the many beaches along Lake Michigan.
TIPS
BEST TIME TO VISIT
Chicago has brutal winters. I recommend a visit between June and September. We traveled there in late September.
GETTING AROUND
As a New Yorker, I especially appreciate the walkability of the city and the option of public transportation. The CTA “L” or elevated subway is the primary means of public transportation and is well-connected throughout the city.
To/From Midway Airport: the CTA “L” orange line makes stops directly at the airport and all over the Loop. It takes around 30 minutes.
To/From O’Hare Airport: the CTA “L” blue line also makes stops directly at the airport and all over the Loop. This will take you about an hour.
Tip: Save locations to a list on Google Maps – your hotel, bars and restaurants, sights, etc. for planning your days efficiently. This will help you see which sights, bars, and restaurants are in the same areas.
COVID-19
With the spread of COVID-19, all travelers should prioritize their health and safety. Rules and restrictions are constantly changing, so stay updated HERE for related rules and restrictions in Chicago.
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