How to Spend 2 Days in Chicago: Ideas for your Chicago Itinerary

It’s crazy that this was my first trip to the Windy City! (I don’t count the trip I did at 9 years old with my aunt and uncle) It was my first time exploring as an adult and with the intent to write about it and I’ve come about with some pretty awesome ways for you to spend 2 days in Chicago. You’ll find on my suggested Chicago itinerary, the must see attractions as well as some off radar spots!

Getting to Chicago

It would be about a 13 hour drive from NYC to Chicago so like most people would,  I opted to fly!  I flew into O’hare International, but there is also Midway Airport nearby. From O’hare Airport you can take the blue line “L” train for about a 45 minute journey into the city. One way cost is $2.50.

If you’re staying in a hotel, always check to see whether or not they provide an airport shuttle and whether it’s complimentary.

Getting Around Chicago

I ended up purchasing a 3 day unlimited Ventra card. The cost of a 3 day unlimited card is $20 and works on both the bus and train. Chicago is definitely not a city where a car would be necessary. Walking and public transit worked out just fine for me with the occasional uber ride.

Where to Stay for 2 days in Chicago

The Best areas to stay in Chicago

  • The Loop
  • River North
  • Gold Coast
  • Magnificent Mile
  • Lincoln Park

double beds in hotel room

Luxury Hotels

  • Four Seasons
  • Waldorf Astoria
  • The Langham
  • Fairmont Chicago–  is overlooking Millennium Park and has an incredible view of Lake Michigan. This Hotel is fully equipped with a fitness studio, Spa and tap room.

Mid Range Hotels

  • Soho House
  • Thompson Hotel– located in the downtown Gold Coast area, The Thomspon Chicago is a trendy and modern hotel with plenty of comfort. Nico Osteria is an Italian restaurant located at the hotel and the food and service was delicious!
  • Kimpton
  • Freehand

Budget Hotels

  • Longman & Eagle
  • ACME Hotel
  • Hotel Felix


breakfast on Hotel bed

What to do during 2 days in Chicago

Check out Millenium Park

If you didn’t go to see Cloudgate a.k.a. The Bean while you’re in Chicago, were you even there? There is plenty to do at the park but the Bean has definitely become one of the top attractions. It’s something you can’t miss when spending 2 days in Chicago.

See a Show at Chicago Theatre 

A variety of music and performances and sporting events are held here so make sure you check the schedule!

2 Days in Chicago

Chicago theatre

Cruise the river with First Lady Boat Cruise

This was one of my favourite activities in Chicago! It was a perfect start to the trip and such a great way to gain perspective and insight into the city, especially if you’ve never been before.

Have a Spa day or morning at Aire Ancient Baths 

Aire Ancient Baths experience in Chicago is unique anything else. You literally feel like you’ve stepped into another world! With no sign of the city at this discreet location you can fully relax. They even have a salt pool (flotarium) with music under the water!



Take in City Views at Sky Deck

The Sky Deck is located in the Willis Tower and features unparraelled views of Chicago. Go out on the ledge for the best shots! Be warned that you do have to queue up and they time you to take pictures but you can go back around if you want more time. I definitely suggest trying to be the first one in to decrease wait time.

Explore the Lakefront Trail

A 18.5 mile pedestrian pavement along the Lake Michigan shores.

Take a walk around Navy Pier 

A Pier on the edge of Lake Michigan with plenty to do. Rides, games, restaurants and more.

Escape the city at Garfield Park Conservatory

FREE to enter (donations encouraged) conservatory with an “L” stop just yards away. Home to all sorts of plants and they even had baby goats when I was there!


Where to Eat and Drink during 2 days in Chicago

Where to Drink

  • Cindy’s Rooftop – A classic Rooftop bar overlooking Millenium Park
  • Beatnik – This globally inspired restaurant had me in my happy place! The lush decor, curated cocktails and inventive food make it a must while in Chicago!
  • The Hampton Social
  • Gilt Bar
Cheers cocktails at Cindy's Rooftop

Cindy’s Rooftop


Where to Eat

  • Safehouse – A spy themed interactive restaurant. Fun for the entire family. This will definitely bring out the kid in you!  I was very impressed with some of the lengths they went to for the theme!
  • Cabra – A cevicheria Peruvian inspired restaurant.
  • The Purple Pig– In the middle of the toursity chaos and tasteless restaurants off Michigan Ave, the Purple Pig stands out.
  • Momo World
  • Pequod’s Pizzeria

Chicago Deep Dish Pizza

  • Burt’s
  • Bartoli’s
  • The Art of Pizza
  • Lou Malnati’s
  • Giordano’s


Check out my Guide to Chicago’s Best Instagram Spots.

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