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Use our Travel forum for recommendations on everything from day trips to the best family-friendly holiday destinations.

Chicago/ Lake Michigan recommendations

23 replies

Makingsenseofitall · 28/12/2025 21:24

we are planning to go next July/ August. Dh, me and two DDs (19 and will have a 21st birthday there). Girls not big drinkers and will want a mixture of active and relaxing. Any accommodation or activity recommendations?

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NewYearNewMee · 28/12/2025 21:32

The architecture river cruises are so good and informative, definitely recommend! See if you can get a baseball game in too, atmosphere is 10/10. Sears tower is a great lookout spot, the Starbucks reserve is really cool too! Pizza wise Pequods is incredible, Giordanos is very good.

How much are you wanting to spend on a hotel?

ella455 · 28/12/2025 21:35

I used to live in Chicago and instead of sears tower I always took all my visitors to Hancock building - bar on the 96th floor. It’s an amazing view , and you can enjoy it with a drink. Visit Lincoln park and east lake view (boys town) neighbourhoods - great vibe, more locals and less tourists compared to the magnificent mile

Makingsenseofitall · 28/12/2025 21:39

@NewYearNewMee thank you so much. Probably a nice hotel for 2/3 nights for the 21st and then perhaps something much more literally lakeside such as a cabin or a self catering place near the edge of the lake?

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Makingsenseofitall · 28/12/2025 21:40

@ella455 that’s so helpful. Thank you so much.

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Serenrose · 28/12/2025 22:00

I also agree with the architectural river cruise. We loved the Art Institute of Chicago and enjoyed visiting the cloud sculpture and the bean at Millennium Park. We also popped into Macy’s.

We were there whilst the Lollapalooza Festival was on and that meant it was super busy around the Millennium Park area and parts of the park were closed off. So you might want to consider avoiding those dates.

Makingsenseofitall · 28/12/2025 22:28

Thank you @Serenrose inwill look up when that is happening

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NewYearNewMee · 29/12/2025 07:35

@Makingsenseofitall there’s a few lovely hotels just by the dusable bridge - the intercontinental there has some great views from the rooms. The Drake at the top of the magnificent mile is more old fashioned but we had some incredible views over Lake Michigan when we stayed there. The Sheraton grand is in a good location too and we’ve always enjoyed our stay, same for the Langham.

Makingsenseofitall · 29/12/2025 07:55

@NewYearNewMee brilluant recommendations. Thank you

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user1471548941 · 29/12/2025 08:19

The Westin at Michigan Avenue is in a fab location. There’s another Westin downtown but we liked this one- it’s on the way to Lincoln Park etc, smack bang on magnificent mile and right on the shores of Lake Michigan. We went in October and could have been in LA with the white sandy beach and blue water, it was a gorgeous spot, a minute from the hotel!

I got a Lonely Planet pocket guide to Chicago and that had some amazing food recommendations for traditional diners and pizza places!

AttilaTheMeerkat · 29/12/2025 09:41

Would second the Art Museum of Chicago and the Magnificent Mile. The Field Museum of Natural History is also worth a visit as is Navy Pier on the waterfront.

The legal age for drinking in Illinois is 21 and proof of age is needed.

AttilaTheMeerkat · 29/12/2025 09:47

The bar on the 96th floor of the Hancock tower sadly closed down in September 2023. There is the Cloud bar on the 94th floor and they have a website.

Makingsenseofitall · 29/12/2025 09:55

Thank yoh for these top recommendations. The one turning 21 doesn’t drink and the 19 year old doesn’t drink much either so I don’t think access to alcohol will be an issue at all. I guess that’s already ‘priced in’ as I wasn’t aware the age to drink alcohol was below 21 anywhere in the US?

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Iwantacampervan · 29/12/2025 13:20

We bought a city pass when we went to Chicago which gave us entry to the museums, boat trips, viewing galleries etc. We also bought a one week travelcard which meant that we could go on the trains, buses etc. I didn't want a small hotel room so booked in an apartment hotel which gave us a lounge (with sofa bed) and a kitchenette as well as a bedroom - a buffet breakfast was included.

Makingsenseofitall · 29/12/2025 13:44

Thank you @Iwantacampervan can you remember which one you booked? Would you recommend it?

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Iwantacampervan · 29/12/2025 14:02

Makingsenseofitall · 29/12/2025 13:44

Thank you @Iwantacampervan can you remember which one you booked? Would you recommend it?

We stayed in the Homewood Suites by Hilton - Downtown (East Grand Ave) - it was 7 years ago but the website looks the same. There is a swimming pool and gym on the top floor. A good location - I would stay there again.

Makingsenseofitall · 29/12/2025 16:11

Iwantacampervan · 29/12/2025 14:02

We stayed in the Homewood Suites by Hilton - Downtown (East Grand Ave) - it was 7 years ago but the website looks the same. There is a swimming pool and gym on the top floor. A good location - I would stay there again.

Thank you. I had spotted those and wondered about them.

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Defender90 · 29/12/2025 16:25

We stayed in the Westin hotel on the river, done the lake and river boat tours, both good.

Lunch on Navy Pier was lovely too.

We only had a few days there as part of Route 66 roadtrip and I would go back to explore more given the chance.

Makingsenseofitall · 29/12/2025 17:29

@Defender90 I really appreciate your recommendations. Thank you

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Maryaliceyoungx · 31/12/2025 10:30

Lake Geneva in Wisconsin is amazing in summer - not far from Chicago.

for Chicago - my top tip is the architecture boat tour. It’s fascinating!

Makingsenseofitall · 31/12/2025 12:41

Amazing @Maryaliceyoungx thank you!

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BitOutOfPractice · 31/12/2025 12:55

The Chicago institute of Art is one of the best galleries I have ever been to and I’ve been to a lot!

avoid the Lincoln park zoo. So many sad and stressed looking animals 😢

Makingsenseofitall · 01/01/2026 17:34

Thank you @BitOutOfPractice really helpful

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BitOutOfPractice · 01/01/2026 19:53

We hired a car and drove to Starving Rock National Park. We all enjoyed that.

And I would highly highly recommend a trip to the baseball. I hardly expected to like it but it was a real highlight of our trip. My adult DDs still talk about it now. Chicago is fabulous!

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