My husband and I love to go on getaways! We don’t live too far from Chicago, so we often do day trips or an overnight trip. I thought I’d put my planning skills to use and write up a getaway itinerary for couples! I’ve researched the best places to eat and fun things to do in Chi town. At the end I also added some extra places worth mentioning in case you don’t like some of the ideas listed.
Start by dropping your bags off at the front desk of the Sheraton Grand. You can check in later in the day. Enjoy a walk to Farmhouse Chicago. This restaurant has some delicious items. I want to try their pretzels and vanilla bean cheesecake with strawberry cider glaze!
After all that yummy food, go shopping on the Magnificent Mile! My hubby likes the Water Tower Place because it has the Lego Store, Cubs Clubhouse and Chicago Sports Museum Store. I like Franseca’s and White House Black Market. Nordstrom Rack is also a must as well as a browse through Tiffany’s & Co. I also like Eately, Saks on Fifth Ave., and Nieman Marcus if there’s time.
Check into your hotel by 3 pm. Take a rest if you need to, but freshen up and change into a nice outfit.
Head to Navy Pier. The views from Navy Pier are gorgeous, and if you don’t mind heights you can ride the Centennial Wheel! We’ve also taken a water taxi across the way to the Shedd from Navy Pier which was a fun experience! After checking out the sites, head to the end where there’s the Miller Lite Beer Tent. On the weekends they have live music starting around 2 pm. Check out their schedule here to see who’s playing! They have a variety of drinks and delicious food. I’m looking forward to trying the beer brats! You should stay here until that golden hour time so you can get some great photos as well!
Take an Uber to Second City by 7:15. Shows usually start at 8pm. This is a fantastic improve comedy club; you and you’re sweetie are bound to laugh! Check out their shows here.
Head back to your hotel for a good nights rest! If you’d rather stay up for some drinks Lizzie McNeill’s Irish Pub is not far from the Sheraton hotel. I always like to find places within walking distance to our hotel later at night. They have delicious drinks and yummy food if you want a snack after the show! Both my husband and I have eaten here a couple of times. Their Rueben and Italian Beef sandwiches are yummy as well as their Bailey’s Irish Cream cheesecake.
In the morning you can order room service for breakfast in bed (they have some delicious breakfast at The Sheraton Grand!). Or get ready for the day and head to Kanela Breakfast Club. They serve Greek and American breakfast and is on the way to your next destination at Navy Pier. If you’d rather something light and a bit quicker you could go to Dollop Coffee Co. on Ohio Street; they have some yummy coffee drinks!
Walk to Milton Lee Olive Park by Oak Street Beach and Navy Pier. There are some gorgeous views of the harbor and city buildings.
Rent Divvy bikes at the Streeter Dr. and Grand Ave location (Navy Pier). It’s $15 for 3 consecutive hours or $3 per 30 minutes. You really will only need it for about 2 hours, but it’s totally up to you. Bike along the Lakefront Trail to Buckingham Fountain, then head to Millennium Park for the famous Bean photo. Drop off your bikes at the Millennium Park Divvy Station first. It’s a bit crowded there and you don’t want to have to worry about the bikes. It’s also quicker to walk from the park back to the hotel then biking.
Freshen up and change for theatre play. There are so many options in Chicago for Broadway plays. We really enjoy the Oriental Theatre as well as the CIBC Theatre. The Oriental Theatre is near Garrett Popcorn (buy afterwards – you can’t take it in!) The CIBC Theater is a block from the Italian Village. There’s also the Apollo Theater in Lincoln Park. We’ve been there, but I would suggest planning a trip around Lincoln Park area for that or just Uber there like we did. (I also have a friends getaway for the Lincoln Park area that would be fun for a couples getaway as well! I love downtown Chicago, but Lincoln Park is a close second for me!)
Walk to Public House for lunch by 12. This gives you an hour and a half to enjoy food and drinks. They have alcoholic milkshakes that look to die for!
Head to your play. Typically plays are at 2 pm in the afternoon. There are also evening shows around 7 or 8pm.
Walk back to your hotel. We like to rest on vacation (afternoon naps are the best when you don’t have any kiddos with you!)
Head to 360 Chicago Observation Deck for some amazing views!
A block from 360 Chicago is Drumbar, a fun rooftop bar. Grab a drink and enjoy the rooftop views. You could also go to The Signature Room at the 95th if you want something a little classier.
Uber to Piccolo Signor, a romantic Italian restaurant, for dinner. Enjoy a relaxing and romantic evening just the two of you! They have a patio outside that would be wonderful for a summer evening.
In the morning, pack your bags and check them in at the front desk to be held. Eat breakfast at Yolk-Streeterville location. This breakfast place comes highly recommended!
Book an architecture river tour that leaves from Lofts At River East on Ogden Slip. There is one that leaves by 10 am.
After the river tour, take a leisure walk along the Chicago river to Catch 35 for a delicious lunch. Check out Veteran’s Park Ledges along the way. They have a Vietnam Memorial.
Catch 35 has some amazing seafood; in my opinion some of the best in Chicago! Some of my favorites: Shrimp & Crab Bisque, George Banks Haddock, George Banks Scallops, and Filet Mignon Medallions. If you decide to stay for dinner instead, their Alaskan King Crab and Filet Mignon is soooooo good! My husband and I like to share the plate and get an extra side (their Parmesan Truffle French Fries are yummy!) And make sure to save room for dessert- their Flourless Chocolate Lava Cake is Heavenly! They also have great sangrias!
Afterwards head back to your hotel, pick up your bags, and head home.
Some other restaurants worth mentioning:
*Italian Village has three different Italian restaurants and is a great location if you’d rather grab lunch or dinner before or after a play. Their plates are so big you can easily share!
*Sweetwater Tavern and Grille is a delicious place to grab dinner. Their Pan Fried Tilapia entrée is delicious as well as their side of asparagus. Their drinks are also delicious. They have a great variety of beers as well as a delicious Peach Cooler cocktail in the summer.
*Wildberry Pancakes and Café is a great breakfast spot.
*Lou Malnati’s Pizzeria…. the BEST pizza ever! There’s also Giordano’s or Chicago Pizza and Oven Grinder are really good too!
A few other date ideas:
*You could do shopping on the magnificent mile, drinks at the Signature Room at the 95th followed by dinner at The Cheesecake Factory (bottom of Hancock tower.) That’s one of our favorite places to eat, but that could be because that’s where we always went in high school when we visited! They do have some delicious cheesecake; my favorites are strawberry and caramel pecan turtle!
*A Cub’s game is always fun – we’ve had many day dates at Wrigley.
*You could book a spa day. The spa at The Four Seasons is pretty amazing.
I hope this helps you plan a fun getaway with your sweetheart!