48 Hours in Chicago: Where to Stay, What To Do & Where To Eat

Ready for a weekend in Chicago? Of course you are! Who doesn’t love to spend time in the Windy City?! Whether you’re looking to pack everything in to one jam packed weekend, or pick your highlights from Chicago’s Top Things To Do, we’ve got options and ideas to suit every budget and every style of traveler. From Museums to Planetariums,  Gangster tours to Signature Bars, you can build your own itinerary to make sure you get the best from your 48 hours in Chicago. And with recommendations for where to stay and what to eat – we’ll have your weekend break to Chicago organized before you know it! Chicago Things To Do

Chicago Things To Do

epic Guide to 48 hours in CHICAGO

– Things To Do, Where To Stay & Where to Eat!

A Guest Post by Alannah McEwan from Itchy Feet Travel

Chicago is the third biggest city in the USA and the fourth biggest in North America so there’s lots of tourist attractions to see and do. So what if you only have 48 hours? How can you make the most of those two days? I’m going to share with you the 10 best things to do in Chicago, suggestions for where to stay and some must try foods to make sure you get the best from your weekend away! Chicago Things To Do

RELATED: Struggling with what to pack? Check out our Ultimate Travel Packing List (with free pdf printable!) to make sure you pack everything you need!



1.    Architecture River Cruise

48 hours chicago things to do where to stay

A great way to see the city and learn some history at the same time is by doing a river cruise. I did the architecture tour and it lasted 75 minutes. I got to see a lot of the city during this tour as well as learn about major events that have shaped the city and the different styles and types of architecture that make Chicago what it is today. It is one of the best Things To Do in Chicago


2.    Magnificent Mile Chicago things to do

48 hours chicago things to do where to stay

A great and free thing to do in Chicago – take a walk down magnificent mile. It’s one of the best know areas of downtown Chicago. The mag mile is 13 blocks that stretches from the Chicago River to Oak Street and is lined with shops, restaurants, and beautiful buildings. This is one of the best things to do in Chicago this weekend.

3.    Navy Pier

48 hours chicago things to do where to stay

Another great place for a walk in Chicago is Navy Pier. In the summer months it’s buzzing with people and energy.  Also, during the summer there are fireworks every Wednesday and Saturday evening. The pier was built 100 years ago in 1916 and is now one of the city’s most popular tourist’s sites. Chicago Things To Do


4.    Millennium Park

best things to do in chicago this weekend - visit the bean!

This 24.5-acre park is packed with attractions. While you’re there check out Frank Gehry’s Pritzker Pavilion and serpentine bridge, sculptor Anish Kapoor’s 110-ton Cloud Gate (also know as the bean) and Jaume Plensa’s Crown Fountain. The Lurie Garden has year-round flower displays and monthly garden walks. Still looking for Chicago things to do? read on


5.    Art Institute of Chicago

36 hours chicago - things to do in Chicago this weekend

There are many museums in the city, but only one that’s been rated by TripAdvisor as the Best Museum in the World. The AIC is the perfect way to enjoy the indoors on a rainy or chilly day. You could easily spend all day here and still not see everything, so if you’re on a time crunch decide which exhibitions interest you the most so that you make the most efficient use of your time. You could even grab a Fast Pass to skip the lines.  Personally, I thought the miniature rooms were pretty cool, the amount of details was unbelievable!


6.    Shedd Aquarium

48 hours chicago things to do where to stay - what to do chicago

The aquarium is 75-year-old institution. Here you will find piranhas, frogs, snakes, rays, turtles, eels, predator sharks and much more! Chicago Things To Do


7.    Signature Room on the 95th Floor

what to do in Chicago

To get an unbeatable view of Chicago head to the Signature Room. It’s on the 95th floor of the John Hancock building. Don’t forget to go to the bathroom where you will get the best view! We probably spent just as much time in the bathroom as we did in the lounge! Definitely one of best things to do in Chicago this weekend and the number one Chicago things to do.

8.    Lincoln Park Zoo Chicago things to do

48 hours chicago things to do - what to do in Chicago

The Lincoln Park Zoo is the oldest zoo in the USA! It is also one of the only free zoos in the country. Here you can see all types of animals from apes to zebras, and overall, the zoo has more than 1,000 animals!


9.     Chicago Mob Tour: Criminals and Gangsters

best 48 hours in chicago things to do where to stay

Escape into the criminal past of Chicago. This Mob Tour will take you to River North, Gold Coast, Lincoln Park, Old Town, and Magnificent Mile districts. You’ll learn about Chicago’s underworld of gangsters and mobsters. Hear stories about Scarface, Al Capone, The Untouchables, and the Chicago Mob.


10.   Adler Planetarium

chicago 48 hours - chicago in 48 hours - 36 hours in Chicago

Go on a trip to the moon at the Adler Planetarium. This was the first planetarium in the United States and includes a real research observatory and a space theatre. There is no need to wonder what to do in Chicago with all these suggestions for the the best things to do in Chicago.


where to stay Chicago

Thompson Chicago - Luxury Stay ($250+ per night)

Strategically located in the heart of the city, this 4-star hotel makes for an ideal base in Chicago. It is located a brief stroll from John Hancock Center Observatory, Chicago Water Tower and Michigan Avenue.
After a day of sightseeing in the region, guests can unwind in the comfort of their air conditioned rooms. They all offer movies-on-demand and a mini bar.
Like more info? Click to Read Trip Advisor Reviews

Westin Chicago River North - Mid-Range Stay ($150-$250 per night)

Conveniently situated, The Westin Chicago River North offers easy access to Chicago's main tourist attractions. It has a spa and wellness centre, as well as a kids club, 24-hour room service and valet parking.
The Westin Hotel River North Chicago features modern rooms equipped with a mini bar, tea and coffee making facilities and a refrigerator. They also offer a range of entertainment amenities, such as movies-on-demand.
Like more info? Click to Read Trip Advisor Reviews
Where To Stay Chicago

Best Western River North - Budget Stay (<$150 per night)

Offering views of Chicago, Best Western River North Hotel is situated close to a popular shopping district, plus boasts a rooftop terrace and an indoor pool. This modern property is conveniently situated in Downtown Chicago.
Attractions near Best Western River North Hotel include Michigan Avenue, the Chicago Theater and Magnificent Mile. Its central location offers easy access to sightseeing, dining and entertainment.
Like more info? Click to Read Trip Advisor Reviews

What and Where to Eat and Drink In Chicago

Enjoying Chicago is as much about what you do as what you eat.  You’ve gotta try these three Chicago favorites:

Deep Dish Pizza

Chicago Things to do where to stay

I asked locals and tourists alike about where to get the best deep dish pizza in Chicago. The two names I heard the most was Giordano’s and Lou Malnati’s. I chose to try Lou’s on my trip. I ordered the calamari fritti, buffalo chicken wings, and of course their famous deep dish pizza with sausage and extra cheese. Everything was tasty and the portions were a good size. The pizza was piled high with toppings and the staff was friendly and attentive. Two thumbs up!


Chicago Style Hot Dog

48 hours chicago things to do where to stay

Next on the list of tasty Chicago things to do is to eat a Chicago style hot dog! I didn’t even realize before my trip that city had their own unique style of hot dog.  This dog is windy city favorite.  Topped with yellow mustard, green pickle relish, tomato, a slice of dill pickle, sport pepper and celery salt. Most important is what’s not on the hot dog … ketchup! The kiosk where I picked up my dog even had a sign that said if you want ketchup you have to dance for it!


Chicago Style Popcorn

48 hours chicago things to do where to stay

For Chicago style popcorn you’ve got to try Garretts. There are several locations in the city, I stopped and got a bag at their Navy Pier location. There is a variety of flavors to choose from. I went for the Garrett Mix, a yummy combination of Caramel Crisp and Cheese Corn. Two great flavors in one bag!



  • Groupon have awesome local deals for Chicago and is updated all the time – from massages and beauty treatments, to dining deals and money off things to do. Check out their local deals and see where you can save some cash on things you already planned to do!
  • Tour search engine Viator offers affordable organized tours to see different parts of Chicago
  • TicketNetwork and SeatGeek list the best events going on in Chicago – see if there is anything special on during your trip!


So there you have it a full run-down of the Top Things To Do in Chicago along with suggestions for where to stay and what to eat. I hope you now have loads of ideas for how best to spend your 48 Hours in the Windy City, and don’t forget to grab these everyday travel essentials before you go:






Oh, and if you enjoyed this article, please pin and share – I’d really appreciate it! Click the P in the share bar for full size images!

Chicago Things To Do     Chicago Things To Do


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48 Hours in Chicago: Where to Stay, What To Do & Where To Eat was last modified: by

Alannah has a serious case of itchy feet and incurable wanderlust! Originally from Canada, she went on her first international trip at the age of fifteen to Paris France. Since then, her passion for travel and adventure has continued to grow. She has currently been to over thirty countries and lived in three. She writes a travel blog where she shares her adventures and travel tips.

Follow her adventures on Facebook, Instagram and Twitter

38 thoughts on “48 Hours in Chicago: Where to Stay, What To Do & Where To Eat

  1. Punita Malhotra says:

    Given a choice due to paucity of time, I know which ones I would definitely not miss…the Art museum and the Chicago Mob Tour. Those would be on my list for sure. And the more of the rest, I could manage to squeeze in, I would.

  2. Gokul Raj says:

    That is a really nice guide. Not sure if I will be able to do all that in 48 hrs but loved the tips on where the stay. I would love the Gangster Tour….have read a lot about that but to see those places in person would be a nice experience.

    • Vicki says:

      Thanks Gok – but on a side note – there is no suggestion that you could do everything on the list, just a guide to what is out there to help you prioritize what fits your interests and needs. But I agree – the gangster tour would be super cool!

  3. Laura Lynch says:

    I’ve only been to Chicago once and really wanted to go back again before we left the U.S., but didn’t make it. I highly recommend that architecture tour. The boat ride is really fun and you get to learn so much about the city along the way.

  4. Christopher says:

    Deep dish pizza, hotdogs and the gangster tour. Love it. This is a great guide and since Chicago is a short flight from Toronto I will definately be doing it in 48 Hours. The river tour would be awesome too. I really can’t wait to visit the Windy City.

  5. Drew says:

    Chicago is such a fun town. I’ve done the architecture river cruise, which was great, especially in one of the prettiest downtowns in the US. I also usually take a stroll through the Cultural Center, which has some truly amazing mosiac ceilings, right in the heart of downtown. Cindy’s Rooftop Bar is a perfect place too to get a bird’s eye view of Millennium Park and Lake Michigan. Not to mention the tasty cocktails!

  6. Efthimis K. says:

    I didn’t know that Chicago has so many nice attractions. I really liked your guide because you have given me so much information in a few words. The bean looks really cool and I would love to visit the AIC and the zoo as well!

  7. Suze says:

    Seeing the Cloud Gate sculpture would be top of my list as it wasn’t there when I visited years ago. I remember going to see the Michael Jordan sculpture though!

    • Vicki says:

      I’d love to see ‘The Bean’ too – such a iconic sculpture! and the Michael Jordan one sounds interesting too – a bit like the Rocky statue in Philly!

  8. Laura says:

    I’ve seen so many pictures of that bean sculpture. I didn’t know it was in Chicago. I’d like to see that and go on a river cruise.

  9. Voyager says:

    It’s so good to know that Chicago has contributed on a great level to the country. Whether it’s the Art Institute of Chicago or the Lincoln Park Zoo or the Adler Planetarium, everything is just fantastic!

  10. Swati & Sam says:

    We pretty much did Chicago on foot. From one park to another museum. Loved clicking the photograph of the Chicago skyline from the Shed aquarium. The view from the Sears tower is completely worth the money and time. A very informative write-up and a great guide.

  11. RaW | Ramble and Wander says:

    Reading this post makes me a bit frustrated because I have a friend who lived in downtown Chicago, who had been bugging me to come and visit him there but I kept putting it off. And now he’s moved to San Francisco! Otherwise I wouldn’t have to worry much about accommodation, haha! Anyways, as someone who’s into architecture, I’d love, love, love to take the architecture river cruise and walk along the Magnificent Mile just to take in all the architectural beauties along the way. That would be my kind of heaven!

  12. Elisa says:

    Chicago is on my wish list since long time, I’d like to go there especially for the architecture. You propose a handy guide with the musts and some interesting tips, will have it in mind (especially the Chicago hot dogs . .) if I ever go to Chicago! Thanks

  13. Nisha says:

    This is what I call a perfect introduction to a new city. New for me , as I have never been there. Anish Kapoors “Bean” is spectacular. I remember seeing his sculpture called “The world upside down” in Israel Museum in Jerusalem.

  14. Tara says:

    I had no idea that the Lincoln Park Zoo was the oldest in the USA. I have experienced most of these gems in Chicago, and it’s one of my all-time favorite cities, especially in the summer.

  15. Mansoureh says:

    I didn’t know there are many attractions in Chicago. I always associated the city with cold and snow. It is because of all the movies I have watched. The hot dog looks interesting. Also, I am in love with popcorn, When I go there I would try Chicago style popcorn too.

  16. G&D Blog says:

    My co-workers were able to visit the Adler Planetarium when they were asked to help to our Chicago Lab, and that made me so jelly. I love to check out that Lincoln Park Zoo with my hubby. Im just hoping that my body can handle the weather there. 😀

  17. Danielle says:

    This is great! We just booked a very last minute long weekend trip – leaving tomorrow! Haven’t done any research on Chicago so this helps a lot!

  18. Mike says:

    Millenium Park and the Bean are so cool to see in person. This is such a great guide to Chicago! I wish I had 48 hours when I visited so I could see it all but sadly I was just passing through.

  19. Natasha Haley says:

    Never been to the states or more specifically Chicago but heard a lot of great things about it. It does look super appealing from these pictures. I never knew they had their own style of hot dog either but I would be making sure I tried that when I went too!

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