Disclosure: I was a guest of the Choose Chicago, but all opinions and recommendations are my own. This post also contains affiliate links.
Despite the fact that Chicago is the third largest city in the United States, I’d only visited once (briefly) before this trip. It’s often skipped by international tourists in favor of the two coasts but after spending 3 days in Chicago during November, I can honestly say that Chicago is a city worth visiting and revisiting – yes, even during the winter.
Admittedly, I was a tad hesitant when Choose Chicago invited me on a holiday-themed trip at the end of November. Not because I wasn’t excited – I was – but because I’m a huge baby about the cold, despite the fact that I’m well-equipped with winter gear after several disastrous cold-weather trips. But I packed by warmest clothing and went on my way. I was surprised to find that Chicago isn’t actually *that cold* in November, so it’s an excellent time to visit and experience all the holiday vibes, virtually nonexistent crowds, and mild winter weather.
Here’s the reality: you can’t see all of Chicago in 3 days. There are too many cool things to do. But, this 3 days in Chicago itinerary is perfect for a first-timer who wants to get a taste of what Chicago has to offer. It’s a tad busy but easy to modify no matter when you’re visiting. So without further ado: the Chicago 3 day itinerary.
Table of Contents
Arrival in Chicago
In an ideal world, you’ll arrive the evening before your first full day in Chicago and get a good night’s sleep. Chicago is easily accessible by various modes of transportation depending on where you’re coming from. I flew into Chicago O’Hare International Airport from Los Angeles, but you can take the train or bus if you’re traveling from the East Coast or Midwest. If you’re planning on flying, be sure to check out Skyscanner to get the best deal on flights.
Should I get a Chicago CityPASS?
Depending on how long you’re planning on staying in Chicago and which attractions you want to visit, you should consider getting a Chicago CityPASS to save money on entrance fees.
In a nutshell, the Chicago CityPASS is a prepaid collection of tickets that will save you 50% off admission to Chicago’s top five attractions. Here’s what you’ll get with the pass:
- Shedd Aquarium – Priority Entry
- Skydeck Chicago – Day/Night Admission
- The Field Museum – All-Access Pass
- Adler Planetarium – Entry + 2 Sky Shows + Atwood Sphere Experience OR Art Institute of Chicago – Fast Pass
- Museum of Science and Industry – Entry + 1 Ticketed Experience OR 360 CHICAGO Observation Deck –Express Entry
The pass is valid for 9 days from when you first use it and can be purchased online. But the big question remains – should you get one? My answer: it depends. The itinerary I’ve included below definitely includes both Skydeck and the 360 Observation deck and some free time for various museums of your choosing. So, you’ll have to do the math. If you plan to visit 3 or 4 of these attractions, then the CityPASS is worth it and you should buy it. If not, then you can pay for the attractions separately. It’s up to you!
Chicago Itinerary: Day One in Chicago
CAFC River Cruise
There’s a reason that the Chicago River Cruise is ranked the #1 tour in Chicago on Tripadvisor – it’s really that awesome, even when it’s cold. Unexpected, right? The cruise I went on (the CAFC River Cruise) is co-run by Chicago’s First Lady Cruises and the Chicago Architecture Center. The tour is 90 minutes long and the volunteer docents are a wealth of knowledge: they shared tons of fascinating stories about the history of Chicago and the buildings along the Chicago River. Plus, there’s both an open deck and a warm, closed deck if you get too chilly. The lower deck serves drinks and snacks and has plenty of windows so you can enjoy the view. If you’re planning a visit to Chicago, don’t miss the cruise!
Read reviews here and book it here.
Note: Tours run from March – November, so if you plan on visiting between December – February, I recommend doing a walking tour of this area instead.
OR
Birth of the Skyscraper – Architecture Walking Tour
If you’re visiting Chicago between December and February, then unfortunately, you won’t be able to do a river cruise (I imagine the river is frozen over). However, you can do an architecture walking tour instead! Free Tours by Foot runs quite a few walking tours with various themes including the Birth of the Skyscraper, which focuses on the innovation and history of Chicago architecture. If architecture isn’t your interest, consider one of their other tours instead. They even have a few special winter tours that take the weather into consideration. Just make sure you tip your guide well – it’s the only “fee” for the tour.
Check out all the tours here and read reviews here.
Lunch at Giordano’s
By the time you’re done with your tour, it will be lunch time. What better food to try than the iconic Chicago deep dish pizza? Giordano’s is just a couple of blocks from the Chicago Architecture Center and serves some of the best Chicago deep dish around (the “best” deep dish is a hotly debated topic, as you can imagine). Giordano’s is well known as one of the originators of “stuffed” pizza – a deep dish with the toppings layered within the pizza then topped with sauce. Prepare to wait around 45 minutes for your pizza to cook (deep dish takes awhile) but the wait is definitely worth it! Address: 130 E Randolph St, Prudential Plaza, Chicago, IL 60601
Read reviews here.
Millennium Park, Maggie Daley Park, and Grant Park
I’m a huge fan of nice public parks and love to spend time in them as much as possible. Millennium Park is easily the most famous of Chicago’s parks, known as the location of Cloud Gate AKA The Bean.
Time to walk the pizza off! Millennium Park is just a couple of blocks from Giordano’s and there’s plenty of things to do in and around it. If you’re visiting during winter, there’s a large, public ice-skating rink with free admission – you just have to pay for rentals. I highly recommend skating if you’re up for it!
Just behind the rink is The Bean. This spectacular sculpture was created by British-Indian artist Anish Kapoor and is a Chicago icon. It’s virtually impossible to get photos here without people in them (unless you go at 6 AM) but it’s fun to see what sort of creative shots people take. Once you’ve gotten your photo(s), keep wandering into Millennium Park: don’t miss the Jay Pritzker Pavilion, the BP Pedestrian Bridge, and the Lurie Garden.
Next, make your way over to Maggie Daley Park, just on the opposite side of the Pedestrian Bridge. This park is more of a park for “play”: they have a rock climbing wall, mini golf, tennis courts and more (open from April – October). However, what *is* open during the winter is the awesome skating ribbon, a circular ice-skating path with the Chicago skyline as its backdrop. SO cool. Although I went ice-skating near The Bean, I think I would have preferred to skate here since the set-up is so unique. Like the other rink, admission is free – you only have to pay for skate rental.
Continue your way south toward Grant Park, home to the spectacular Buckingham Fountain. The fountain is on from May – October, so you can easily skip Grant Park if you’re in Chicago during winter. However, if you’re there during summer or fall, it’s well-worth a visit to see the evening lights and take some cool photos. Plus, there’s a 20-minute water display every hour on the hour that’s not to be missed.
Note: If you’re traveling to Chicago during winter and it’s too cold to spend time in the park, I recommend visiting one or two of the CityPASS attractions: The Shedd Aquarium, The Field Museum, The Art Institute, or The Adler Planetarium.
Dinner at The Dearborn
Located just a short walk away from the parks is The Dearborn, a stylish New American restaurant run by two Irish sisters. The food is fresh, seasonal, hearty, and absolutely delicious. I was there with a group and we ended up ordering nearly every appetizer on the menu plus mains and desserts, so I can say with confidence that all the food is drool-worthy. The standouts include the fried chicken, the hush puppies, and the fries, but in all honesty, we didn’t eat a single bad dish. What really made The Dearborn a standout restaurant wasn’t just the mouthwatering food, but also the exquisite service. Our waiter was incredibly patient and kind, answering all of our questions, joking around with us, and ensuring we got our dishes in a timely fashion. If you’re looking for a spectacular and reasonably-priced restaurant after your first day of exploring, this should be it! Plus, if you end up staying at LondonHouse like I did, it’s only a ten minute walk away.
Read reviews here.
Santa Baby Pop-up Bar (optional)
If you happen to be in Chicago between mid-November and early January, I highly recommend visiting a Christmas-themed pop-up bar – specifically, Santa Baby.
I don’t celebrate Christmas or drink but I adore a good theme and Santa Baby did not disappoint. The decor was completely over the top in the best way possible with ornaments adorning the bar and tables, lights and stockings hanging from the ceiling and Christmas music playing in the background. The bar courtyard has an impressive Christmas display and inside they serve both food and drinks. I loved that they had plenty of outrageous non-alcoholic drinks as well.
Chicago takes the holidays very seriously and there are quite a few pop-up bars in this neighborhood during the holidays. It’s a really cool and unique Chicago experience and the bar is actually open during the daytime for under-21-year-olds who want to visit. SO cool!
Check it out here.
Day Two in Chicago
Helicopter Ride
Before visiting Chicago, I’d never been in a helicopter before. If you’ve always wanted to do a helicopter tour, Chicago is a pretty awesome place to do it, thanks to its amazing skyline. It’s such a cool experience to be able to see the city from above. I went at night and loved the views (plus they have a special ‘holiday lights’ tour from the end of November to early January!) but for photo purposes, I recommend taking the morning flight (night photography plus movement = shaky photos). Either way, you’re guaranteed an exhilarating flight and a unique view of Chicago.
Book it here.
OR
Museums Using CityPASS
If a Chicago helicopter ride isn’t up your alley, consider using your CityPASS to visit one of the many cool museums that are included on the ticket. Here’s a quick overview of where you can go:
- Shedd Aquarium – The Shedd Aquarium brings you face to face with marine life from all over the world; they have everything from penguins to octopus to Beluga whales; it’s truly impressive! I often hesitate to recommend zoos / aquariums because of animal rights concerns, but Shedd was actually the first U.S. aquarium to receive the Humane Conservation credential by American Humane for the excellent care and welfare of their animals. So feel free to visit and marvel over sea life to your heart’s content.
- The Field Museum – Chicago’s natural history museum contains over 40 million specimen and artifacts – how crazy is that? SUE, the world’s most complete Tyrannosaurus rex, is easily the biggest draw, but there are tons of different extinct animal exhibits as well.
- Adler Planetarium – Boasting over half a million visitors per year, the planetarium is the go-to place for all things Space in Chicago. In fact, it was the first planetarium in the United States. Don’t miss The Atwood Sphere (included in the CityPASS), a steel sphere with holes that maps the night sky.
- OR Art Institute of Chicago – If you’re an art lover of any kind, I highly recommend a visit to The Art Institute. You can easily spend hours exploring all the different exhibits; they have everything from Picasso to Warhol. Be sure not to miss the Thorne Miniature Rooms – they’re exquisite!
Note: Both The Skydeck and The 360 CHICAGO Observation Deck are part of my recommended itinerary, which is why I didn’t include them in your options.
Lunch at Au Cheval
Okay, so here’s the deal. Au Cheval doesn’t take reservations, which means if you’re in a big group and it’s peak time, you’re waiting for the long haul. I don’t believe in waiting more than half an hour to eat somewhere so if the wait is insane, save it for another visit. But if it’s not, then by all means, go and eat what many people say is the best burger in America. I know, right?! That’s a BIG statement. I regret not going myself but I totally trust fellow foodie, Kimly, who was with me on this Chicago trip and said it was amazing. Read reviews here.
If you can’t get in, consider lunch at Girl & the Goat instead, another Chicago icon known for its internationally-inspired, very creative small plates. The good news is that this restaurant does take reservations…you just have to make them far in advance. Read reviews here.
Either way, there are plenty of amazing restaurants in the West Loop, so don’t despair if you can’t get into either spot. Monteverde, Cabra, and The Publican are all great spots nearby.
Wndr Museum
Honestly, I’m not a big museum person. There are a few specific kinds of museums I enjoy, but I rarely visit cities and recommend museums unless they go above and beyond. But the Wndr Museum is easily one of the coolest museums I’ve been to in the last few years, which is why I added it to this itinerary. One of the walls in the museum says “sight / sounds / smell / taste / touch / wndr” and this exactly exemplifies what this museum is all about: an amazing sensory experience that will fill you with a sense of wonder and delight. Yes, I’m aware of how cheesy that sounds, but it’s true. It’s totally interactive and just FUN – there are really no other words to describe it. If you only visit one museum in Chicago, make it this one!
Read reviews here.
Navy Pier
At first glance, Navy Pier is an All-American shopping center on a pier. And while that’s *technically* what it is, there’s more to Navy Pier than meets the eye. This iconic part of Chicago’s skyline has plenty of cool things to do and see, starting with riding the Centennial Wheel for epic views of Lake Michigan (don’t worry, it’s heated!). There’s also a virtual reality experience, climbing walls (closed during winter), and more. During the winter, the fun moves indoors and turns into The Winter Wonderfest, which has rides, activities and photo ops. Plus, there’s the Winter Wonder Market, which is open from the end of November until Christmas Eve. No matter what time of the year you visit, this is a cool place to hang out and explore.
Check it out here.
Dinner at Offshore
Located at the end of Navy Pier, Offshore is the nation’s largest rooftop venue, offering panoramic views of Lake Michigan and the city skyline. It has both an enormous outdoor terrance and a gorgeous, 36,000 square foot interior with giant glass windows for some seriously epic lighting during the day and stunning views at night. Design aside, the food here was spectacular – the menu has quite an impressive variety of fusion food: everything from shareable apps and snacks to large plates. The food is amazing but the ambiance really elevates the Offshore experience – I highly recommend eating here if you visit The Navy Pier!
Read reviews here.
360 Observation Deck
Am I overdoing it by recommending multiple Chicago observation decks? That would be a no because the skyline is epic (and all the views are a little different). The 360 Observation Deck entrance fee is actually included in the CityPASS and the deck doesn’t close until 11 PM, so it’s the perfect place to visit after dinner. Located on the 94th floor of the John Hancock Center, 360 CHICAGO offers breathtaking views of Chicago’s skyline, the lakefront, and four states. It’s also less crowded than Skydeck. But what really makes 360 stand out is the thrill ride, TILT. TILT is a moving platform that literally tilts visitors over the edge of the building – it’s mildly terrifying, extremely exhilarating and an experience like no other. And yes – you should definitely pay the extra $7 for TILT.
Note: The main entrance fee is included in the CityPASS but you can also purchase tickets separately here.
Day Three in Chicago
Gangsters and Ghosts Tour
Chicago was notoriously run by criminals and mobsters back in the day and you can learn all about this sordid side of history during the Gangsters and Ghosts Tour! This 2 hour walking tour takes you through various parts of The Loop, where you’ll visit Chicago’s most haunted spots and hear terrifying tales of legendary gangsters such as Al Capone, John Dillinger and more. I personally nerd out about criminal history so if you’re anything like me, you’ll love this tour. It’s quite a unique thing to do in Chicago.
Book it here.
Note: If this isn’t your speed, consider visiting one or two of the CityPASS attractions: The Shedd Aquarium, The Field Museum, The Art Institute, or The Adler Planetarium.
Lunch at Christkindl Market OR Chicago Hot Dog
If you’re visiting in November or December, then make your way to the Christkindl Market for lunch, an authentic German Christmas market with tons of delicious things to eat and drink and plenty of beautiful handicrafts to buy. For lunch, munch on yummy German treats like raclette (bread topped with melted cheese), kartoffelpuffer (potato pancakes), schnitzel (deep-fried meat), and more. Don’t forget to sample some of the delicious desserts and hot chocolate as well.
Check it out here.
If you’re visiting after Christmas (or just like, any other time during the year), now’s your chance to try a famous Chicago hot dog! A true Chicago hot dog is a sausage topped with mustard, onions, relish, pickle, tomato, sport peppers and celery salt, all in a hot dog bun. Like deep dish pizza, the “best” Chicago hot dog is fiercely debated but for the sake of location, I recommend Devils Dawgs on State. The hot dogs are all-beef (woo!) and there are quite a few options for those that want different toppings. Address: 767 S State St, Chicago, IL 60605
Read reviews here.
Skydeck
No trip to Chicago is complete without a visit to the top of the tallest building in the Western Hemisphere – Skydeck Chicago! Located on the 103rd floor of the Willis Tower, your views don’t get any better than this (unless you’re taking a helicopter ride, of course). Besides incredible 360-degree views spanning up to 50 miles, one of the coolest parts of the Skydeck is The Ledge – a glass balcony extending just over 4 feet outside the building (there are three). You’ll feel like you’re walking on clouds and get the coolest photos ever (I mean…look at my photo). So fun!
Note: the Skydeck admission is included in your CityPASS but you can purchase tickets separately here.
Choose Your Own Adventure: Museums or the Magnificent Mile
The rest of the afternoon is yours to do as you please. Consider using your CityPASS to check out any of the remaining spots you wanted to visit or head to The Magnificent Mile for a little shopping and exploring. The Magnificent Mile is the 13-block stretch of North Michigan Avenue that runs from the banks of the Chicago River to the south, to Oak Street to the north. Here you’ll find plenty of shops, restaurants, hotels and attractions – think a one-stop shop for everything you’ve ever wanted to purchase. Consider visiting the largest Starbucks in the world, The Starbucks Reserve Roastery, where you’ll find everything from coffee to food to baked goods to cocktails. Otherwise, simply wander and take in all the sights. Or, if you’re feeling tired, head back to your hotel for a nap. You’ve got plenty of options.
Dinner at Frontera Grill
There’s a reason that Frontera Grill has won so many awards. Its chef, Rick Bayless, isn’t just known for modern Mexican cuisine, he literally has a tv show about it. So, he knows Mexican food well and this is reflected in the delicious menu at Frontera Grill. Frontera Grill is Bayless’ first restaurant in Chicago and is totally worth the hype – everything from the pozole to the flautas to the tacos are heavenly and I say this having been to Mexico twice and growing up in Southern California. If amazing Mexican food is what you’re after, Frontera Grill is the place to be. And yes, you should make reservations ahead of time. Read reviews here.
Second City (optional)
If you still have some wind left in you, consider catching a show at Second City, Chicago’s first improv theater. This comedy theater has launched the careers of many famous comedians including Tina Fey and Amy Poehler so you know their shows are quality. They usually have multiple shows per day but you’ll have more luck catching an evening show if it’s the weekend, so plan accordingly and buy tickets ahead, of course.
Read reviews here.
Additional Activities and Recommendations
If you’re spending four or even five days in Chicago, I’ve got you covered. Here are a few extra things I did while I was in town (or would have liked to do) that could easily be added to an itinerary.
- Christmas Tree at Millennium Park: If you’re in Chicago during the holidays, be sure to stop by Millennium Park in the evening to check out the huge, lit-up Christmas tree. It’s beyond spectacular.
- The Walnut Room: The Walnut Room is located inside the Macy’s on State Street and is the first restaurant opened in a department store. It’s totally decked out during the holidays, complete with a ginormous Christmas tree and fairies prancing around granting wishes. If you get a chance to eat here, do it! Check it out here.
- Art on theMART: Located along The Riverwalk between Wells and Lake St., Art on theMART is a permanent public art installation – the longest-running and largest digital art projection in the world. Art is projected on the buildings nearly ever night after sunset, showcasing both local and international works. Such a cool initiative! Check it out here.
- Garfield Park Conservatory: If you can’t get enough of nature, don’t miss a visit to Garfield Park Conservatory, a 184-acre botanical conservatory on Chicago’s West Side. While there, be sure to stop by Inspiration Kitchens, a nearby restaurant / chef-training facility run by a non-profit combating homelessness. It’s a great way for your tourism dollars to support people who are learning in their kitchens and building the foundations to overcome homelessness and poverty. Check out the restaurant and the conservatory.
- Chicago Cultural Center: The Chicago Cultural Center is the nation’s first free municipal cultural center. Opened in 1897, this stunning building has truly magnificent architecture including two majestic stained-glass domes. Plus, admission is free so why wouldn’t you visit? Check it out here.
- Catch a game at Wrigley Field: I’m not a big sports person but Chicagoans take The Chicago Cubs very, very seriously. So if it’s baseball season, consider going to a game and cheering on the team!
- Eat your way through the city on a Chicago Food Tour: Discover Chicago’s food, history, architecture and culture on this 3-hour, small-group walking tour. You’ll sample six of the Windy City’s quintessential staples and are guaranteed to leave full and a lot more knowledgeable about Chicago’s food scene. Book it here.
- The Chicago Theater Tour: The Chicago Theater is an icon of the city and what better way to enjoy it than with a behind-the-scenes tour? This one-hour guided tour covers the theater’s architecture, history, and famous performers throughout the years and is a must for theater lovers! Book it here.
- See a live theater show: Broadway might be the most famous theater district in the country but Chicago’s scene certainly holds its own, with an impressive number of productions at any given time. But hey, why pay full price when you can get discounted tickets? Hot Tix offers half-price tickets to a wide variety of Chicago theatre productions. Check ticket availability here.
- Explore other neighborhoods: There’s more to Chicago than The Loop and Downtown so why not get out and explore the other neighborhoods? Wicker Park, Boystown, Lincoln Park and Chinatown, to name a few, are all worth exploring. So if you have some extra time, check out the areas outside of the center.
Where to Stay in Chicago
If it’s your first time in Chicago, I highly recommend staying in or around The Loop, the neighborhood where Millennium Park is located. A large majority of places you’ll be visiting are in this area and are easily accessible by foot. I specifically recommend LondonHouse Chicago, the hotel I stayed at. It couldn’t have been more perfect. The location was walking distance from pretty much everywhere, but was on the north end of The Loop so I didn’t have to deal with any noise or crowds. The service exceeded expectations with everyone going above and beyond to ensure my stay was wonderful. And the rooms were beautifully designed, with detailed touches that made me feel ultra pampered. Plus, the rooftop has epic views of the city (as do the rooms). LondonHouse definitely gets my stamp of approval.
Alternatively, my other recommendations are below:
HI Chicago Hostel (Backpack)
If you’re all about that backpacker life, HI Chicago Hostel is the best hostel to stay in. Located in The Loop, this environmentally-friendly hostel has everything you’ll need: gender-segregated dorms, mixed dorms, private rooms, towels and linens, a game room and more. Breakfast is included and there’s a communal kitchen. To top it all off, they offer guided tours of the city and plenty of activities. What more could you need?
Read Tripadvisor reviews | Book a Stay
Cambria Hotel Chicago Loop (Budget-Friendly)
For accommodation that’s central and doesn’t break the bank, stay at the Cambria Hotel. This comfortable hotel features clean, modern rooms, a game room, onsite parking and a fitness center. The service is excellent and the prices are incredibly reasonable as well.
Read Tripadvisor reviews | Book a Stay
LondonHouse Chicago (Mid-Range)
I stayed at LondonHouse Chicago while I was in Chicago and loved it. It’s definitely an upgrade from “standard” accommodation but still on the affordable side. This boutique hotel is located in a historic building and has some seriously spectacular views of the Chicago Riverwalk. The beds were so comfortable I didn’t want to leave and the dining here was superb, as well (having tried both the main restaurant and the food at the rooftop bar). I already raved about this hotel earlier so I won’t keep going but in all honesty, if you’re looking for an excellent place to stay in Chicago, LondonHouse is it!
Read Tripadvisor reviews | Book a Stay
The Peninsula (Splurge)
If you want to treat yourself, there’s no fancier place than The Peninsula. I mean, it was recently named the 2nd best hotel in the country. So you know it’s spectacular. This luxury hotel boasts beautiful and comfortable rooms with plenty of natural light, a temperature and lighting control console, a spacious tub, and both fitness classes and an indoor swimming pool. Did I mention it has near-perfect scores on Booking.com? That’s pretty impressive!
Read Tripadvisor reviews | Book a Stay
Transportation in Chicago
Getting around Chicago is pretty straightforward. A lot of my favorite sights and activities were in and around downtown, making walking my preferred mode of transportation. However, if the weather sucks or you’re not spending time in the downtown area, I recommend taking public transportation. The CTA (Chicago Transport Authority) network of trains and buses is incredibly well-connected and easy to use (thanks Google Maps!). Uber is also an option but the cost can add up pretty quickly.
If you decide to use the public transit system for a majority of your trip, I recommend picking up a reloadable Chicago Ventra Card that you can use for riding public transport. You can buy it online or from a machine. Easy peasy.
What to Pack for Chicago During Winter
It’s no secret that Chicago is cold during the winter. I was lucky and the coldest temperature I had to deal with was in the 20s Fahrenheit, but temperatures in Chicago can drop to below zero. Dress warmly and in layers. In fact, I’ve written an entire blog post on how to pack for winter travel, which you can read here. Read it, study it, live it. I’ve learned from trial and error, trust me. The most important tip I have for you is lots and lots of layers!
So how many days you should spend in Chicago? I’d say at least a week to explore the city and surrounds. So, while a 3 day trip to Chicago certainly isn’t enough to do everything, it offers a great overview of this spectacular city. I know I’ll be back for more.
Tell me: have you ever been to Chicago? What’s your favorite place in the city?
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