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Destination Chicago: A Weekend in the Windy City

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Planning a weekend in Chicago? Our guide provides insider tips on where to stay, where to eat, what to do, and so much more!

A Weekend in Chicago: What to do, where to stay, what to eat, and more |

I started out this new series with Palm Springs and when I was deciding where to go next I realized I should take you all along to the place I know best. Buckle up for a quick tour around my adopted hometown. This week we are planning out a weekend in Chicago!

Spring and fall are my two favorite seasons here in the Windy City. (FYI, Chicago isn’t called the Windy City because of the actual breezes, but because of our windy politicians!) Lots of other people love summer in Chicago, so I wouldn’t discount that either, but I find that the humidity can be pretty wretched so if you have a say over when to visit I would recommend a weekend in Chicago anytime between March-June or September-October. Of course, if you come in the summer and it gets a little steamy we do have Lake Michigan right there that you can jump into when you need to cool off!

Here's everything you need to know about visiting Chicago, including what to eat in Chicago, where to stay in Chicago and more |

How to get to Chicago

Chicago has two main airports, Midway and O’Hare, so flying here is usually easy and direct flights can be obtained from much of the country. Pretty much every airline flies into Chicago, though not all airlines fly into both airports. For instance, Southwest Airlines only flies into Midway.

Chicago is the midwest hub for Amtrak, so getting here by train is relatively easy as well. I’ve traveled via train to New York City, Washington DC, and even out to California and it can be a relaxing way to travel. It’s not the way to go if you’re short on time though and only coming for a weekend in Chicago! The train moves slow and frequently gets delayed, especially if you’re coming from Michigan.

Finally, both MegaBus and Greyhound travel to Chicago from quite a few different locations around the country.

Once you’re here, one of the great things about Chicago is that you don’t need to rent a car. Chicago is very walkable, but there’s also a great public transportation system by way of the subway (called the “el” here – short for elevated train), buses, or even the commuter train system, Metra. Then, of course, you have your choice of Taxis, Uber, or Lyft.

Tip: Uber frequently offers free credits! If you haven’t used Uber before, do a quick search to see if you can find some credit before booking your first ride! Use my referral link here and you’ll get $15 off your first ride, though I’ve sometimes seen better offers than this available!

Chicago Theatre

(Image via Dimitry B.)

Where to stay in Chicago

According to Trip Advisor, these are some of the best hotels in Chicago:

I haven’t personally stayed at any of these hotels and I’m going to go out on a limb and say they’re not exactly the most budget-friendly since they’re the best hotels in a big expensive city! We’ve stayed at a few hotels downtown, though, and I personally recommend these options:

  • Kinzie Hotel – A gem of a hotel, Kinzie Hotel is upscale but budget-friendly and within walking distance of much of the city. It’s also dog-friendly! Check out my Kinzie Hotel review for more details.
  • Hard Rock Chicago – The location doesn’t get much better, as this hotel is right on Michigan Avenue and within walking distance of pretty much everything.
  • Hotel Chicago Downtown (a Marriott hotel) – This is a surprisingly affordable hotel in the heart of downtown.
  • Omni Chicago Hotel – All of the rooms here are suites and this hotel is also right in the thick of everything as it’s located right off of Michigan Avenue in the heart of the main shopping district.

Because we have dogs and recently stayed downtown with them, I also know of two dog-friendly hotels in Chicago, just in case you happen to be traveling with (wo)man’s best friend:

  • The Blackstone (a Marriott hotel) – also on Michigan Avenue, but pretty far south, it’s still within walking distance to most things although it could be a bit of a hike
  • W Chicago – I haven’t personally stayed here but I do know that W hotels are notoriously dog-friendly

Home & Room Rental

If you’re looking for something a little homier than a hotel, you might want to check out, where you can rent someone’s actual home from them. Two other popular options are Airbnb and Homestay, where you rent extra rooms that people may have available or, with Airbnb, their entire home.

Renting an entire home or apartment can be an incredibly budget-friendly way to stay in Chicago, especially if you’re traveling with a large group.

Renting an extra room and staying with the homeowner will definitely save you money and you might even make some new friends!

Please note that home and room rentals are generally considered safe, but I highly recommend reading the reviews before committing to stay anywhere, as well as doing your homework to ensure that you’re staying in a safe neighborhood.

What to eat in Chicago: Chicago Style Hotdog

(image via Jeffreyw)

Where to eat in Chicago

I could probably write a novel about where to eat in Chicago, but instead, I’ll just share a few of my absolute favorite restaurants.

Pequods Pizza (2207 N. Clybourn Ave.) – If you’re visiting Chicago for the first time, or heck, anytime, you’re probably going to want some Chicago style pizza. Though the tour guides will probably tell you to check out places like Pizzeria Uno or Gino’s East, the best Chicago style pizza is at Pequods Pizza. The thing that makes their pizza better than all of the rest? They caramelize the crust, which really takes it to the next level. The only downside is that if you’re staying downtown you’ll probably need to take a cab to get there. If you’d prefer to eat downtown then I’d say Lou Malnati’s is a close second.

Siena Tavern (51 W. Kinzie St.) – Siena Tavern was developed with Chef Fabio Viviani from Top Chef, and you’ll get some of the best Italian food in Chicago at this restaurant. I’ve been here a few times, taken many out-of-town visitors here and have never had a bad meal.

Quartino (626 N. State St.) – I hesitate to add ANOTHER Italian restaurant to this list but what can I say? Chicago has great Italian food! Quartino is downtown but you probably won’t find it listed as a stand-out in the travel guides. What I’ve found after 12 years of living in Chicago though is that this restaurant is secretly a favorite of the locals. You’re always going to get a good meal here.

Gibsons Bar & Steakhouse (1028 N. Rush St.) – Chicago is also a big steak city and Gibsons is one of the most iconic steakhouses. Do you watch The League? Gibsons is where they meet up on the show.

Mexique (1529 W. Chicago Ave.) – Mexique was developed by another Top Chef alum, Chef Carlos Gaytan. To be honest, we have only been here for brunch but we return frequently because the food is that good. I mean, it is so good that they were awarded a Michelin Star in 2013! They serve a Mexican French fusion cuisine, so the items at Mexique are pretty unique.

Portillo’s (100 W. Ontario) – If you want to try a good Chicago-style hot dog – yellow mustard, chopped white onions, bright green sweet pickle relish, a dill pickle spear, tomato, pickled sport peppers and a dash of celery salt and absolutely NO ketchup – Portillo’s is a great place to get one. Also, do yourself a favor and get an order of their amazing fries as well as a chocolate cake milkshake. Yum!

Do-Rite Donuts (50 W. Randolph St.) – Donuts are all the rage in Chicago right now, but I think you’ll find Chicago’s best donuts at Do-Rite. The Chocolate Glazed and Candied Maple Bacon are a-maz-ing.

Vosges Haut-Chocolat (520 N. Michigan Ave.) – I talk about my love of Vosges all the time on this site, so if you’re coming to Chicago I highly recommend checking them out! Even if you don’t buy anything they almost always have samples available. And, if for some reason you forget to add this to your itinerary, there are a couple of Vosges stands at O’Hare Airport. 😉


Cloud Gate in Chicago, aka The Bean

What to do in Chicago

Chicago isn’t lacking for entertainment options, that’s for sure! I feel like I take some of Chicago’s amenities for granted since I live here, but if you’re coming here for the first time, these are some of the activities I’d suggest checking out.

The Second City - Some of the world’s best comedians have called The Second City home at one point or another, including Tina Fey, James Belushi, Dan Aykroid, Bill Murray, Bob Odenkirk, Steve Carrell, Stephen Colbert, Amy Poehler, Jane Lynch, and many, many more. This is the place to see them before they make it big, plus, the comedy is absolutely hilarious (obviously).

Architecture Boat Tour – If the weather is cooperating, an architecture boat tour on the Chicago River where they explain the history of some of the buildings comprising the magnificent Chicago skyline is a must-do and a nice, relaxing way to pass the time.

Take in a Cubs Game – OK, let me be up front. I lived in Wrigleyville for a couple of years and I now have a passionate and irrational hatred for the Cubs. My husband says I should direct my ire at their fans and not the team itself but that is clearly nonsense. Regardless of my personal feelings, even I can recognize that Wrigley Field is pretty awesome and full of history so if you’re in town when the Cubs are playing you should totally try to get tickets.

Tip: Cubs tickets are notoriously hard to come by when the team is playing well, so for discounted Cubs tickets, be sure to check out StubHub! You can often find great deals on this site, and many tickets are now available via PDF, so you can receive them almost instantly!

Shopping – This pretty much goes without saying, right? Chicago is a great city for shopping. What I will say is that while tourists typically flock to Michigan Avenue, I actually enjoy the shopping on State Street a little more. You’ll find a lot of the same stores, including the original Marshall Field’s (now Macy’s) but smaller crowds.

Explore the Neighborhoods – While downtown Chicago is great and you won’t run out of things to do during a weekend visit, Chicago is also comprised of some pretty awesome – and walkable – neighborhoods! The area comprising Ukrainian Village/ Wicker Park/ Bucktown is fantastic for shopping, food, coffee, etc. Lincoln Park, and especially its namesake park, is a great place to visit. There’s even a free zoo in Lincoln Park! I could go on, but there’s plenty to explore if you want to escape the downtown area.

Check Out a Museum – I know there are some people who will tell you to visit every museum when you visit a new city, but I am not one of those people. I rarely visit museums when I’m on vacation because I’d rather be out walking and exploring. That said, Chicago does have some great museums so if you want to spend some time indoors you can’t go wrong at the Art Institute of Chicago or the Museum of Science and Industry.

Visit Millennium Park – If you’re coming to Chicago then I assume Millennium Park, home of Cloud Gate (aka “The Bean”), is already on your list. A picture with The Bean is a must-have souvenir! (Bonus: Visiting Millennium Park and snapping a pic with the Bean is FREE!)

Get a Good View of the Skyline – In my opinion, the best view of the Chicago skyline can be found on the museum campus. To find my favorite, head to Adler Planetarium. (You probably won’t want to walk there, but it’s doable.) The Planetarium is right next to the lake, but the land juts out just enough to give you the best view of the Chicago skyline.

See a Show – Depending on how long you’ll be in the city, you might want to try to see a play or musical. Chicago has a thriving performing arts scene, and original productions at Steppenwolf Theatre Company and the Goodman Theatre are always worth checking out. Chicago also receives its fair share of visiting musicals, and the Tony Award-winning musical Hamilton will soon begin an open run here! Tip: Check out Goldstar for discounted theater tickets in Chicago!

Tip: To save money on tourist attractions in Chicago you might want to get a Chicago CityPass. For $98 you will get VIP admission to five of the top attractions in Chicago, including Shedd Aquarium, Skydeck Chicago, The Field Museum, Museum of Science and Industry OR 360 Chicago, and Adler Planetarium OR Art Institute of Chicago. Another option is the Go Card Chicago, which lets you purchase tickets to Chicago attractions from your smartphone. When you purchase two or more attractions you’ll save 20%!


Where to shop in Chicago

Chicago has a great cultural scene, an amazing sports scene, incredible food and it’s also one of the best cities in the country for shopping! I polled a few of the most fashionable bloggers in Chicago to get some of their insider tips on where to shop in Chicago.

Yanira Garza

Website: • Instagram: YaniraGarza23

Textile Discount Outlet (2121 West 21st Street)

Yanira: “I am a huge lover of vintage and thrift. Some of my best pieces have been $6 finds. However, I like to make things my own so if I find a skirt I love, I might update the zipper or swap out buttons on a low budget jacket to give it a high-end feel. For trinkets like that, you’ll do no better than this place. Rooms and rooms of fabric but go upstairs to dig through boxes of tassels, notions, and trimmings.”

Beatnix Chicago (3400 North Halsted Street)

Yanira: “I discovered this place in high school and I still wear the gray velvet blazer I picked up there. While the upstairs is a fun room of colorful wigs, Ben Nye makeup (also where I was introduced to bold color), and Halloween assortment, this place also holds a unique assortment of vintage goods. If you don’t mind digging around, you’re sure to find a hidden gem here.”

Intermix (40 East Delaware Place, 841 West Armitage Avenue & 1633 North Damen Avenue)

Yanira: “While not unique to Chicago, it is a great place to try designers you may not find elsewhere in the city. Veronica Beard, Marissa Webb, and Cushnie et Ochs, amongst others, can be found here. Their sales are also amazing. You could get a pair of Sergio Rossi boots for a fraction of the price after season.”

Nikia Jefferson

Website: Chicago Tribune • Instagram: Chitown_fashion

Sir and Madame (5225 South Harper Court)

Nikia: “Owned by husband and wife team, Brian and Autumn Merritt, Sir and Madame is the perfect store for all the ‘cool kids’ in Chicago. From clothing to accessories, their merchandise (which is a good mix of their private label and other indie brands) is street wear for the fashionably conscious shopper. With their ‘classic with a twist’ aesthetic, not only will you find items that will make a statement, but those same items will also become your wardrobe staples time and time again.”

Luxury Garage Sale (1658 North Wells Street)

Nikia: “Luxury Garage Sale is the place that every girl’s designer dreams are made of. It’s a consignment store, but as soon as you step foot inside their Old Town location (or even their 900 Shops location), you feel as though you are walking into a high-end boutique. The designer selection is so well-curated, you can’t go wrong with any purchase. And yes, while they do carry expensive brands like Chanel, Louis Vuitton, and Hermes, you can still find some affordable treasures, particularly in their vintage accessories section.”
The Silver Room (1506 East 53rd Street)

Nikia: “The Silver Room has been a Chicago staple for 20 years! It is known for both its outstanding jewelry collection (which is heavily stocked with wares from local artisans) and its community events. Obviously, they carry some of the best sterling silver jewelry in the city. However, you can also find great pieces in a host of metals and materials, including brass, leather, and wood. After almost 18 years in Wicker Park, The Silver Room is now located in Hyde Park, where it continues to be a one-stop shop for those looking to purchase a unique gift, discover a new artist or pick up a new hobby (hello, French classes!).”

Cheryl Leahy

Website: All Dressed Up with Nothing to Drink • Instagram: CJAllDressedUp

Beatnix Chicago (3400 North Halsted Street)

Cheryl: “This thrift shop right in the heart of Boystown has a little bit of everything. From cowboy boots to faux fur jackets to inexpensive costume jewelry, this store is jam-packed with unique pieces that you won’t find anywhere else.”

Luxury Garage Sale (1658 North Wells Street)

Cheryl: “If you aren’t the type to pick through mountains of thrift pieces, head to this expertly curated upscale designer consignment boutique. You can pick up a coveted quilted Chanel bag for a fraction of retail, or a pair of Christian Louboutins in mint condition.”

Aldo Outlet (1212 North Ashland Avenue)

Cheryl: “This is a true outlet store with incredible deals- you often find items for 50% or more off original prices. It is easily accessible from the Blue Line (Division Stop), but make sure to go during off-peak times because the associates have to get your correct size from the back room. Make sure to check out the accessories and bags as well as the shoes!”

Uniqlo (830 Michigan Avenue)

Cheryl: “This Japanese retailer opened their first Midwest store in Chicago, and it has been incredibly popular with the tagline “Made for All.” This brand has researched fabric technology and produces items with extra capabilities like heat retention or moisture-wicking. Men- grab their signature oxford cloth button-down shirts. Women- shop cashmere sweaters under $100.”

Katie Schuppler

Website: • Instagram: KSStyleConsulting

Jax & Debb (1849 West North Avenue)

Katie: “A great place for men to shop with great customer service. This store is especially great if you are looking to express your personal style.”

Sara Jane  (1343 North Wells Street)

Katie: “A perfect place in Old Town to shop with your girlfriends or just for yourself! The options for work, play, and date night are endless.”

Lori’s Shoes (824 West Armitage Avenue)

Katie: “A women’s shoe heaven in the heart of Lincoln Park. Lori’s caters to a wide range of clients, whether it’s price, comfort, or style you are shopping for they are sure to have it.”


What to wear in Chicago

What should one wear in Chicago? Layers!

OK, during the dog days of summer you probably won’t need to wear layers. But it’s good to be prepared during any other time of the year.  It can get cool at night or if you’re out on the lake, and unless it’s July or August there’s always a chance that winterish weather might appear late or show up early.

The important thing to keep in mind if you want to do a weekend in Chicago is that you’re going to want to wear comfortable shoes! Walking up and down the Magic Mile, plus walking through the stores, museums, or anywhere else you wind up will really put a toll on your feet! Also, I really recommend a crossbody bag or a tote bag. Keep your hands free during your shopping extravaganza!

Chicago is a great city to visit because it’s about as laid-back as a major city can be. There’s plenty to do, whether you enjoy sports, shopping, or being outside. If you’re coming for a weekend or longer, there’s plenty to keep you busy!

For even more Chicago suggestions, check out my new ebook, The Insider’s Guide to Chicago.

The Insider's Guide to Chicago by Lisa Koivu

The book contains insider tips on things like Chicago Fire filming locations, where you’ll find Chicago’s celebrity chefs, free activities to do in Chicago with children and much more!

Be sure to check out:

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Travel Hacks: Shopping for Cheap Flights - - Book your next flight for less using these tips!

This Post Has 2 Comments
  1. Hi. Lisa. Thanks for the nice Chicago CityPASS shout-out in your story. And the photography in your piece is stunning; a visual treat. ~ Deborah Wakefield, CityPASS

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