So you love Grant Achatz and you want to schedule a dinner at the restaurant that propelled him to fame--we empathize. Getting into Alinea can be a challenge (though less so post-COVID). Their online reservation system can be hard to navigate. A date might look available, but then you click on it and you find it's an available wait list. If you can't find a time during your stay, I recommend joining their Facebook group where they post week-of availability. Another option is going to Next or Aviary. Both are Grant's brain-children and much easier to get into.
Cocktail molecular gastronomy is the name of the game at Aviary. It's a Grant Achatz bar/restaurant and worth every penny you spend. Rachel once visited The Aviary the same night as Katy Perry. :) It was quite a night.
The best Cuban food in Chicago, and maybe the US. This is a go-to spot for Rachel and is also the location of Drew and Rachel's first in-person date. :) Bonus: You can explore Roscoe Village, Rachel's neighborhood, after you eat.
Fabulous French restaurant that features a broad selection of wine. This is one of Rachel's favorites as well. Drew and Rachel went here on a date and had one of the best beef tenderloins they've ever had. Bonus: The company has donated to Rachel's nonprofit, PicDiversity. Double bonus: their back patio is enchanting.
Stephanie Izard's Girl and the Goat began back in 2010 and has truly exploded in respect and popularity. The Girl and the Goat features a quirky, earthy menu with combinations you didn't know you needed. The goat series in Chicago now includes Girl and the Goat, Little Goat, and Duck Duck Goat. Little Goat is a cute, yet elevated, diner experience. Rachel promises it has the best Old Fashions in town (even compared to the one at The Aviary).
Overwhelmed by all the great foodie options in Chicago? TimeOut Market is your answer. It's a conglomeration that includes 18 of Chicago's highest-rated chefs under one massive roof (think Agora). You order your meal(s) from a dining counter and then eat in a communal center. It's the most cost-effective way to sample some of Chicago's best chefs. Highly recommended for Sunday brunch. Pre-COVID, this was a favorite of Rachel, Colleen, and Claude.
This is a recent addition to the Chicago-scene and the location of one of Rachel and Drew's first dates as COVID opened up. It is the only southern cuisine that gets Rachel's approval in the city. Their cocktails are literally on fire.
A favorite of both Rachel and Drew, this Peruvian restaurant understands not just the Pisco Sour, but proteins marinated and cooked to perfection. Rachel and Drew enjoy the Lomo Saltado and Empanadas. If you go in person, they have a fantastic second floor deck.
If you know the full engagement story, then you know about Temporis. This is the Michelin-star restaurant where Drew planned to propose. Fate had another plan in mind, but their menu and wine pairing will not disappoint you.
Need some hoops, Pac Man or air hockey in your life? This is the place. You might end up challenging 10-year-olds to a basketball contest as Rachel and Drew once did on a date, but you will not regret the inevitable loss coming your way.
When people talk about Chicago's art scene, the Art Institute is at the head of the conversation. From Degas to Hockney, the museum features historic and memorable art. Bonus: If you're really nice to Rachel, Colleen or Claude, they can get in at least one person with their memberships.
Just north of the Lincoln Park Zoo, this beautiful botanical oasis features plants and flowers from around the world. It sits at the top of Lincoln Park making a day excursion well worth your time and effort. Bonus: Can you find the dinosaurs in the fern room?? They're hidden in the foliage. It should also be noted that the botanical garden is right above Lincoln Park Zoo. Both are free.
There are many companies offering architecture tours in Chicago, but if you haven't done one on a previous trip, this has to be on your list. Chicago has been very strategic with it's skyline and a boat tour down the river is one of the best activities the city has to offer. The top of Sears Tower has nothing on this.
This is tourist central, but with cause. This is a fun and lively pier that features shops, restaurants, and its famed carousel. Walking around the pier is also an option, and one that Drew and Rachel enjoy.
It's touristy for sure, but one of Rachel and Drew's favorite breakfast spots. The pricing is reasonable and they offer a wide array of selections including a separate gluten-free menu (gf cinnamon buns anyone?). Drew and Rachel hope to find a hidden local brunchery, but so far none have compared to the Egg Harbor Cafe (at least in Streeterville).
Another tourist breakfast joint, but a great tourist breakfast joint. Yolk is one of Rachel's favorite breakfast locations--it gets the job done. You can definitely split one of their massive omelets between two people.
This is Drew's go-to breakfast place. Is it the maple bacon or the cream burrata? That's hard to say, but it is delicious and worth your time to visit.
One of the best free options in the city--walking along the lakeshore is a great way to both exercise and enjoy the beautiful Chicago skyline. There are beaches along the way so if you have time, you can grab a swimsuit and towel and spend a day on the beach. The Lakeshore path is a total of 18.5 miles long. You can access it from Navy Pier or really anywhere downtown if you just go East.
You can literally jazz-up your trip to Chicago with this event. It's free and runs Sept. 1-4. While it is all over the city, it is primarily centered at Millenium Park which is walking distance from the W. While you're there, you can also stop and get a selfie at the Bean.
Fresh from Lake Michigan, this festival features the best fresh-water lobster's around. Just kidding. The lobster are flown in from Maine, but that in itself is a kind of a tribute to Drew and his Maine roots. The event only happens once a year and if you're not from Maine, this may be a great way to enjoy some fantastic shellfish.
If you can't get into Alinea, this should be NEXT on your list. Right next door to Aviary, Next is a culinary delight from Grant Achatz.
This is a great shopping, dining, or drinking experience from Mario Batali. You can dine at themed restaurants (e.g. Fish, Pasta, etc.) on the second level, or grab a cup of gelato while you shop Italian food imports.
Immersive experiences have exploded in popularity and the Wondr Museum is one of Chicago's greatest offerings in this space. Full of bright, glowing, edgy photographic experiences, you won't want to go here alone.
This is Central American-inspired cuisine at its finest. It's located in Logan Square and offers a great patio. It's pretty undiscovered so you will definitely beat the tourist crowds with a visit here. RSVP req.
This is the only recommendation in Wicker Park, but this James Beard award-winning bar does not disappoint. Their cocktails are one-of-a-kind in a setting that feels like a velvet dream. This is also one of Rachel's first bars to visit in Chicago. After you have a drink, you can also explore the hipster epicenter that is Wicker Park.
A historic hotel, with a fabulous rooftop bar. This should be on your to-do list. Although it's in a hotel, it gets visited more by locals than tourists.
There aren't a lot of hotel bars on this list, but this one is worth mentioning. It's a collection of three great opportunities: Cira, Cabra and Ladybird. If you're exploring West Loop this is an opportunity to continue the adventure.
It's a little cliche to add this to the list, but it is unfortunately a Chicago staple and fun time. London House drips in elitism (note: its physical address is simply "London House"), but it makes up for it with great views of the city, fun lighting, and great cocktails. This listing is for the rooftop.
If you love blues and jazz, get yourself to this bar asap. It's been around since 1907 and continues to be an iconic Chicago staple. You will need your ID and a cash cover.
Off the radar of tourists, this is a popular jazz and blues bar for people in the know. It's in Logan Square so it could be paired with an outing to Casa Yari.