Chicago.
Your Pick.
Two hotel options in the heart of downtown Chicago — plus private rental options for the crew that wants their own space. Same great city, different vibes.
Choose Your Stay.
⚠️ Prices are subject to change until payment is made. No ground transfers included — it’s cheaper to Uber or bus it downtown with your group once you arrive. All packages include round trip Southwest flights HOU → MDW and hotel stay.
🚗 Ground Transfer Tip: Skip the individual Ubers — when you arrive, split one Uber or hop the bus downtown with everyone in your group. Way cheaper and faster than booking separate rides.
Downtown Chicago location with everything you need for the weekend. Full package includes round trip Southwest flights HOU → MDW and hotel stay. Walk to the Magnificent Mile, the Riverwalk, and everything the city has to offer.
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AC Hotels by Marriott brings that sleek, modern European-inspired design to downtown Chicago. Stylish rooms, great common spaces, and the Marriott quality you can count on. One of the best price-to-quality options on this list.
Or email Petty: pettytravelagent@gmail.com
The Royal Sonesta brings upscale full-service hospitality to downtown Chicago. Elevated rooms, premium amenities, and a sophisticated atmosphere that makes the whole trip feel like more of an occasion. The luxury pick on this list without the luxury price tag.
Or email Petty: pettytravelagent@gmail.com
Wacker at Michigan — it doesn’t get more central than this. Club Quarters puts you at the intersection of two of Chicago’s most iconic streets, steps from Millennium Park, the Riverwalk, and the Magnificent Mile. The location on this one is unmatched on this entire list.
Or email Petty: pettytravelagent@gmail.com
Boutique hotel in River North — one of Chicago’s most vibrant neighborhoods for nightlife, restaurants, and galleries. The Kinzie brings personality and style to a location that already has both. Perfect for the couple or group that wants character over corporate.
Or email Petty: pettytravelagent@gmail.com
The Mart is one of Chicago’s most iconic landmarks — and this Holiday Inn IHG property puts you right there. Solid brand reliability, downtown location, and a price that makes sense for what you’re getting. Great for groups that want the IHG rewards points and a trusted name.
Or email Petty: pettytravelagent@gmail.com
Three ways to get this handled. You decide how involved you want to be.
Use the “View Hotel” links on each option above to book directly. All hotel options include flights and ground transfers as listed.
Use The Links Above →Petty builds a custom TripLink page for your Chicago trip — one shareable link with everything your crew needs to book themselves. No repeated questions, no group chat chaos.
Get TripLink — $59 →Everything done for you from start to finish. Hotels, flights, itinerary, all handled. Your group won’t be calling you with the dumb questions. You just show up. Don’t delay on this price.
Petty Takes Over — $300 →🔍 Already found something on your own? Send Petty the link and she’ll vet it for $25 before you book. → Vet My Trip — $25
Get On Petty’s List.
Trip drops, deal alerts, and group trip tips before anyone else sees them. No spam — just the real ones who plan and actually go.
✈️ Subscribe To Petty⚠️ Breakfast not included in all options — check each card. Prices based on double occupancy.
💡 Save more with 3–4 to a room. Prices are based on double occupancy but you can fit up to 4 comfortably with a pull-out couch or co-sleeping. More people = lower per person cost. Just let Petty know your preference.
Works for both Chicago and New York. Pick the hotel first — then pick how you want Petty involved.
Use the “View Hotel” links above. All packages include flights and transfers as listed per option. You handle the booking — we made finding it easy.
Use The Links Above →Petty builds a shareable page for your trip. One link — your whole crew reads everything, books themselves, no repeated questions in the group chat.
Get TripLink — $59 →Everything done for you — hotels, flights, transfers, excursions, itinerary. Your group won’t be blowing up your phone. You just show up.
Petty Takes Over — $300 →🔍 Not sure if something is the right fit? Send Petty the link and she’ll vet it for $25 before you book. → Vet My Trip — $25
Get On Petty’s List.
Trip drops and deal alerts before anyone else hears about them.
✈️ Subscribe To Petty