Search Deals onChesterton Vacation Packages
Chesterton Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Save 100% on your flight
Price was $425, price is now $234 per person
$234
per person
Jan 20 - Jan 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Sheraton Grand Chicago Riverwalk
Price was $1,389, price is now $377 per person
$377
per person
Dec 20 - Dec 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy 3 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Trump International Hotel & Tower Chicago
Price was $1,664, price is now $945 per person
$945
per person
Nov 27 - Dec 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Hotel Felix River North/Magnificent Mile
Save 100% on your flight
Price was $444, price is now $261 per person
$261
per person
Jan 13 - Jan 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Location was great. Front desk staff were friendly and helpful
Reviewed on Oct 26, 2026
Level Chicago Fulton Market
Save 100% on your flight
Price was $690, price is now $406 per person
$406
per person
Jan 1 - Jan 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
The stay was everything I love the view and peaceful. Thank you
Reviewed on Oct 26, 2026
Hotel Saint Clair- Magnificent Mile
Save 100% on your flight
Price was $453, price is now $281 per person
$281
per person
Dec 4 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Great place! Great location!
Reviewed on Oct 26, 2026
The Talbott, Autograph Collection
Save 100% on your flight
Price was $734, price is now $465 per person
$465
per person
Dec 4 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
It’a a beautiful and charming building with just the right amount of modernity.
My room was a tad bit smalller than I’d expected (queen bed) and the view was nonexistent but cozy and comfortable for for a single person. The room came with a fully stocked mini fridge, a Nespresso
machine and two very plush bath robes.
The staff was very accommodating and friendly. Each day I was there(three), housekeeping was excellent
Shopping, dining and spectacular architecture are in ample supply right outside your door. Will definitely stay here when I’m there city!
Reviewed on Oct 26, 2026
Pendry Chicago
Price was $575, price is now $374 per person
$374
per person
Dec 28 - Dec 31
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Chesterton Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Chesterton Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Tue, Nov 17 - Wed, Nov 18
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$143 Roundtrip, found 2 hours ago
$143
Roundtrip
found 2 hours ago
Sat, Dec 26 - Wed, Jan 6
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$224 Roundtrip, found 1 day ago
$224
Roundtrip
found 1 day ago
Thu, Nov 19 - Sat, Dec 5
LAX
Los Angeles Intl.
MDW
Midway Intl.
$252 Roundtrip, found 2 hours ago
$252
Roundtrip
found 2 hours ago
Tue, Nov 10 - Mon, Nov 30
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,147 Roundtrip, found 6 days ago
$1,147
Roundtrip
found 6 days ago
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