Prairie District Holidays

Photo by Susie Morgan

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Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was €5,523, price is now €4,697 per person
€4,697
per person
1 Oct - 7 Oct
just found
Return direct flight included
Athens (ATH) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)
We booked a two bedroom unit, but the unit clearly wasn't intended for a 2 bedroom. It was obviously a sitting area or something with a bed squeezed in. There was no vent so it made it impossible to shut the door, but then it was open to the living space and a full wall of windows. In addition, they list housekeeping as an amenity, and advertise one day or long term stays, however, for our 4 night stay, this didn't get housekeeping services. Meaning we had to get towels and coffee each day from the front desk, had piles of trash from cooking and such, and a heap of dirty towels from the week. Staff was friendly, but not really provided agency or capacity to do anything to fix the experience. Even a request for a fan to try to cool the space was impossible for them to solve (although they certainly had one for the front desk to keep staff comfortable).

Reviewed on 14 Jul 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was €6,131, price is now €5,273 per person
€5,273
per person
1 Oct - 7 Oct
just found
Return direct flight included
Athens (ATH) to Chicago (ORD)
9.6/10 Exceptional! (1,910 reviews)
We loved our "upgraded" room with the beautiful view of the river, Lake Michigan and the Saturday night fireworks! This was thanks to Michael, our concierge or check-in man at the front desk. It took us a little while to figure out all the lighting but that was a small thing. The coffee at your restaurant left a little to be desired - it was not hearty enough or warm enough. The cappuccino we replaced it with was very good! All in all, a very happy experience.

Reviewed on 14 Jul 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was €5,626, price is now €4,842 per person
€4,842
per person
1 Oct - 7 Oct
just found
Return direct flight included
Athens (ATH) to Chicago (ORD)
9.2/10 Wonderful! (1,136 reviews)
Excellent location. Staff very nice. Room big and bed very comfortable. But noisy. As is all of Chicago. Trying to sell in room soap products for exorbitant prices tachy as hell. Rooftop lounge had sadly very short hours and limited open days. Seems a shame to waste such an opportunity.

Reviewed on 14 Jul 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was €5,500, price is now €4,878 per person
€4,878
per person
1 Oct - 7 Oct
just found
Return direct flight included
Athens (ATH) to Chicago (ORD)
9.2/10 Wonderful! (1,323 reviews)
The check in was seamless. Lobby spotless. Room was very clean and tidy. Rooftop area was super.

Reviewed on 12 Jul 2026

Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Downtown Chicago
Price was €5,458, price is now €4,885 per person
€4,885
per person
1 Oct - 7 Oct
just found
Return direct flight included
Athens (ATH) to Chicago (ORD)
9.2/10 Wonderful! (1,388 reviews)
Beautiful hotel with nice city views. Friendly staff. So many hidden fees, doubled the cost.

Reviewed on 12 Jul 2026

Where to stay in Prairie District

Find the best Prairie District areas and neighborhoods for the activities you enjoy most. Learn more about Prairie District
A busy city street with tall buildings, a bus, and cars.

Downtown Chicago

5 out of top 10 points of interest in this area

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Find hotels in Downtown Chicago

Top hotels in Prairie District

Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is €169 per night from 3 Aug to 4 Aug
€169
3 Aug - 4 Aug
includes taxes & fees
8.8/10 Excellent! (2,850 reviews)
"Rooms are clean and check-in process was smooth. Staff are very nice and polite"

Reviewed on 15 Jul 2026

Hyatt Regency O'Hare Chicago
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is €171 per night from 27 Jul to 28 Jul
€171
27 Jul - 28 Jul
includes taxes & fees
8.2/10 Very good! (1,744 reviews)
"Front desk person were very r"

Reviewed on 15 Jul 2026

The Chicago Hotel Collection Ambassador Gold Coast
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is €274 per night from 26 Jul to 27 Jul
€274
26 Jul - 27 Jul
includes taxes & fees
9.2/10 Wonderful! (1,913 reviews)
"Staff was fantastic and always ready to help; from the front door to the room door!"

Reviewed on 15 Jul 2026

Omni Chicago Hotel
See all 4,364 properties in Prairie District
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much does a Prairie District holiday package cost?
We make it simple for everyone to travel, with Prairie District holiday packages starting from as low as €4,697. You'll have the flexibility to bundle your preferred hotels, airlines and car rental. For the ultimate getaway, why not add some activities and tours to your travel itinerary?
How do I get a cheap travel package to Prairie District?
One of the simplest ways to save cash (and time) is to combine your bookings with Expedia. Hotels, rental cars, flights and activities — we've got them all covered. Pick and choose the combination that best suits you and watch your savings stack up. We know a travel package is never one-size-fits-all. That's why we offer over 550 partner airlines and 1,000,000 properties globally, which lets you customize your Prairie District holiday.
Where should I stay in Prairie District?
Most visitors to Prairie District put both McCormick Place and Millennium Park on their bucket lists. Why not choose a hotel that's close to these great attractions?
How far in advance should I book my Prairie District holiday?
Your safest bet is to book early. Airlines typically advertise flight tickets nearly 12 months prior to departure, and this is a perfect opportunity to score some of the cheapest prices. Just been told you need to take your holiday time next month? No sweat. Expedia are never short on fantastic deals to whisk you away on the getaway of your dreams, at an affordable price.
What does an Expedia Prairie District travel package include?
Expedia has all you need to lock in Prairie District escape, but how you structure your package depends on you. Pick from a combination of flights, rental cars and hotels. Chasing some tours or experiences to keep you on the go? Once you've made your booking, you can add them too. Whatever your budget, there's a deal to meet your needs.
What should I know before booking a Prairie District travel package?
Locking in all the parts of your getaway together is an excellent way to save. Bundle your car rentals, airfares and hotels into one package. But your options don't end at hotels. Expedia features all sorts of properties, including holiday rentals such as beach villas and serviced residences. You've got choices galore!
Can I choose my airline with a Prairie District Expedia holiday package?
Yes, you're in charge. We have access to over 550 partner airlines across the globe, so you can tailor your Prairie District escape according to your needs and budget.
If I'm not able to travel, can I cancel my Prairie District holiday package?
Your situation can change in a flash, so yes, you can. You may be able to cancel and rebook your Prairie District holiday package for free within 24 hours of booking. For older bookings, you can still make changes, but your car rental company, airline or hotel may charge a fee. Want more information? Check out our Customer Service Portal. We're here to help make sure your getaway goes off without a hitch.

Stay near popular Prairie District attractions

Glessner House Museum

You can spend time exploring the galleries in Glessner House Museum during your trip to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theatre scene.
See properties

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

€21
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

€40
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
Art Institute of Chicago

Art Institute of Chicago

€35
per adult
92% of travellers recommend
Art Institute of Chicago
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.